{"id":"https://openalex.org/W3003287708","doi":"https://doi.org/10.1002/chem.202000484","title":"Late\u2010Stage 18 O Labeling of Primary Sulfonamides via a Degradation\u2013Reconstruction Pathway","display_name":"Late\u2010Stage 18 O Labeling of Primary Sulfonamides via a Degradation\u2013Reconstruction Pathway","publication_year":2020,"publication_date":"2020-01-30","ids":{"openalex":"https://openalex.org/W3003287708","doi":"https://doi.org/10.1002/chem.202000484","mag":"3003287708","pmid":"https://pubmed.ncbi.nlm.nih.gov/32003092"},"language":"en","primary_location":{"id":"doi:10.1002/chem.202000484","doi":"https://doi.org/10.1002/chem.202000484","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202000484","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://doi.org/10.26434/chemrxiv.11553597","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5061055809","display_name":"Sean W. Reilly","orcid":"https://orcid.org/0000-0002-1656-1895","observed_orcids":["https://orcid.org/0000-0002-1656-1895"]},"institutions":[{"id":"https://openalex.org/I1285764155","display_name":"Merck & Co., Inc., Rahway, NJ, USA (United States)","ror":"https://ror.org/02891sr49","country_code":"US","type":"company","lineage":["https://openalex.org/I1285764155"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Sean W. Reilly","raw_affiliation_strings":["Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA"],"raw_orcid":"https://orcid.org/0000-0002-1656-1895","affiliations":[{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]},{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5113534932","display_name":"Frank Bennett","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I1285764155","display_name":"Merck & Co., Inc., Rahway, NJ, USA (United States)","ror":"https://ror.org/02891sr49","country_code":"US","type":"company","lineage":["https://openalex.org/I1285764155"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Frank Bennett","raw_affiliation_strings":["Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]},{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5025112191","display_name":"Patrick S. Fier","orcid":"https://orcid.org/0000-0002-6102-815X","observed_orcids":["https://orcid.org/0000-0002-6102-815X"]},"institutions":[{"id":"https://openalex.org/I1285764155","display_name":"Merck & Co., Inc., Rahway, NJ, USA (United States)","ror":"https://ror.org/02891sr49","country_code":"US","type":"company","lineage":["https://openalex.org/I1285764155"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Patrick S. Fier","raw_affiliation_strings":["Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA"],"raw_orcid":"https://orcid.org/0000-0002-6102-815X","affiliations":[{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]},{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5082454092","display_name":"Sumei Ren","orcid":"https://orcid.org/0000-0002-5163-0489","observed_orcids":["https://orcid.org/0000-0002-5163-0489"]},"institutions":[{"id":"https://openalex.org/I1285764155","display_name":"Merck & Co., Inc., Rahway, NJ, USA (United States)","ror":"https://ror.org/02891sr49","country_code":"US","type":"company","lineage":["https://openalex.org/I1285764155"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Sumei Ren","raw_affiliation_strings":["Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]},{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5036948355","display_name":"Neil A. Strotman","orcid":"https://orcid.org/0000-0002-5350-8735","observed_orcids":["https://orcid.org/0000-0002-5350-8735"]},"institutions":[{"id":"https://openalex.org/I1285764155","display_name":"Merck & Co., Inc., Rahway, NJ, USA (United States)","ror":"https://ror.org/02891sr49","country_code":"US","type":"company","lineage":["https://openalex.org/I1285764155"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Neil A. Strotman","raw_affiliation_strings":["Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA"],"raw_orcid":"https://orcid.org/0000-0002-5350-8735","affiliations":[{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc.  Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]},{"raw_affiliation_string":"Department of Process Research &amp; Development, MRL Merck &amp; Co., Inc. Rahway NJ 07065 USA","institution_ids":["https://openalex.org/I1285764155"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5061055809"],"corresponding_institution_ids":["https://openalex.org/I1285764155"],"apc_list":{"value":4000,"currency":"USD","value_usd":4000},"apc_paid":null,"fwci":0.9848,"has_fulltext":false,"cited_by_count":15,"citation_normalized_percentile":{"value":0.67798313,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":93,"max":97},"biblio":{"volume":"26","issue":"19","first_page":"4251","last_page":"4255"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13561","display_name":"Chemical Reactions and Isotopes","score":0.9810000061988831,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},"topics":[{"id":"https://openalex.org/T13561","display_name":"Chemical Reactions and Isotopes","score":0.9810000061988831,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10683","display_name":"Mass Spectrometry Techniques and Applications","score":0.008100000210106373,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12189","display_name":"Sulfur-Based Synthesis Techniques","score":0.0035000001080334187,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/sulfonamides","display_name":"sulfonamides","score":0.8870000243186951},{"id":"https://openalex.org/keywords/stable-isotope-labeling","display_name":"stable isotope labeling","score":0.7329999804496765},{"id":"https://openalex.org/keywords/celecoxib","display_name":"celecoxib","score":0.8029999732971191},{"id":"https://openalex.org/keywords/drug-labeling","display_name":"drug labeling","score":0.5820000171661377},{"id":"https://openalex.org/keywords/green-chemistry","display_name":"green chemistry","score":0.41200000047683716}],"concepts":[{"id":"https://openalex.org/C2781039511","wikidata":"https://www.wikidata.org/wiki/Q3208529","display_name":"Sulfonamide","level":2,"score":0.7156479954719543},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7043458223342896},{"id":"https://openalex.org/C13934619","wikidata":"https://www.wikidata.org/wiki/Q2198720","display_name":"Isotopologue","level":3,"score":0.6674402952194214},{"id":"https://openalex.org/C145782189","wikidata":"https://www.wikidata.org/wiki/Q628025","display_name":"Deamination","level":3,"score":0.6300649642944336},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.587364673614502},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.49610933661460876},{"id":"https://openalex.org/C2777977315","wikidata":"https://www.wikidata.org/wiki/Q7243056","display_name":"Primary (astronomy)","level":2,"score":0.491910457611084},{"id":"https://openalex.org/C2779679103","wikidata":"https://www.wikidata.org/wiki/Q5251805","display_name":"Degradation (telecommunications)","level":2,"score":0.4893781542778015},{"id":"https://openalex.org/C207001950","wikidata":"https://www.wikidata.org/wiki/Q141124","display_name":"In vivo","level":2,"score":0.4745562672615051},{"id":"https://openalex.org/C36674120","wikidata":"https://www.wikidata.org/wiki/Q370228","display_name":"Isotopic labeling","level":2,"score":0.43480461835861206},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.33425065875053406},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.29961085319519043},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2734542489051819},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.12246653437614441},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.06814026832580566},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.0},{"id":"https://openalex.org/C150903083","wikidata":"https://www.wikidata.org/wiki/Q7108","display_name":"Biotechnology","level":1,"score":0.0},{"id":"https://openalex.org/C76155785","wikidata":"https://www.wikidata.org/wiki/Q418","display_name":"Telecommunications","level":1,"score":0.0}],"mesh":[],"locations_count":5,"locations":[{"id":"doi:10.1002/chem.202000484","doi":"https://doi.org/10.1002/chem.202000484","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.202000484","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},{"id":"doi:10.26434/chemrxiv.11553597","doi":"https://doi.org/10.26434/chemrxiv.11553597","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.11553597","pdf_url":null,"source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},{"id":"doi:10.26434/chemrxiv.11553597.v1","doi":"https://doi.org/10.26434/chemrxiv.11553597.v1","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.11553597.v1","pdf_url":null,"source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},{"id":"pmid:32003092","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/32003092","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry (Weinheim an der Bergstrasse, Germany)","raw_type":"Journal Article"},{"id":"pmh:oai:figshare.com:article/11553597","doi":null,"is_oa":true,"landing_page_url":"https://figshare.com/articles/Late-Stage_18O_Labeling_of_Primary_Sulfonamides_via_a_Degradation-Reconstruction_Pathway/11553597","pdf_url":null,"source":{"id":"https://openalex.org/S4377196282","display_name":"Figshare","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4210132348","host_organization_name":"Figshare (United Kingdom)","host_organization_lineage":["https://openalex.org/I4210132348"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Text"}],"best_oa_location":{"id":"doi:10.26434/chemrxiv.11553597","doi":"https://doi.org/10.26434/chemrxiv.11553597","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.11553597","pdf_url":null,"source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},"sustainable_development_goals":[{"score":0.807699978351593,"id":"https://metadata.un.org/sdg/12","display_name":"Responsible consumption and production"}],"sustainable_development_goals_aurora":[{"score":0.41999998688697815,"id":"https://metadata.un.org/sdg/12","display_name":"Responsible consumption and production"}],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":36,"referenced_works":["https://openalex.org/W39215153","https://openalex.org/W258674570","https://openalex.org/W1554241314","https://openalex.org/W1656095725","https://openalex.org/W2006730025","https://openalex.org/W2009883054","https://openalex.org/W2009950869","https://openalex.org/W2011387524","https://openalex.org/W2020630954","https://openalex.org/W2029405633","https://openalex.org/W2030253332","https://openalex.org/W2034711387","https://openalex.org/W2048601647","https://openalex.org/W2069887352","https://openalex.org/W2072259643","https://openalex.org/W2146632301","https://openalex.org/W2151902404","https://openalex.org/W2191749535","https://openalex.org/W2239806434","https://openalex.org/W2321011582","https://openalex.org/W2336773168","https://openalex.org/W2395303858","https://openalex.org/W2554002362","https://openalex.org/W2582103379","https://openalex.org/W2582170638","https://openalex.org/W2746618491","https://openalex.org/W2766234355","https://openalex.org/W2795282638","https://openalex.org/W2887760653","https://openalex.org/W2910172604","https://openalex.org/W2947017011","https://openalex.org/W2952881930","https://openalex.org/W4233928450","https://openalex.org/W4236662555","https://openalex.org/W6603104078","https://openalex.org/W6820954841"],"related_works":["https://openalex.org/W2327787936","https://openalex.org/W3172780936","https://openalex.org/W1964682831","https://openalex.org/W2034456397","https://openalex.org/W4381611341","https://openalex.org/W4247564574","https://openalex.org/W193737498","https://openalex.org/W1555302402","https://openalex.org/W2287981203","https://openalex.org/W2886289776"],"abstract_inverted_index":{"A":[0],"late-stage":[1],"18":[2,36,88],"O":[3,37,91],"labeling":[4,107],"approach":[5,54],"of":[6,22,48,58,101,142],"sulfonamides":[7],"that":[8],"employs":[9],"the":[10,15,23,49,63,99,139],"corresponding":[11],"unlabeled":[12],"molecule":[13],"as":[14],"starting":[16],"material":[17],"was":[18,28,70,118],"developed.":[19],"Upon":[20],"deamination":[21],"sulfonamide,":[24],"a":[25,45,79],"sulfinate":[26],"intermediate":[27],"isotopically":[29],"enriched":[30],"using":[31,128],"eco-friendly":[32],"reagents":[33],"H":[34],"2":[35],"and":[38,69,112],"15":[39],"NH":[40],"3":[41,131],"(aq)":[42],"to":[43,60,121],"afford":[44],"M+5":[46,134],"isotopologue":[47],"parent":[50],"compound.":[51],"This":[52,116],"degradation-reconstruction":[53],"afforded":[55],"isolated":[56],"yields":[57],"up":[59],"96%":[61],"for":[62,105,108],"stable":[64],"isotope":[65],"labeled":[66],"(SIL)":[67],"sulfonamides,":[68],"compatible":[71],"with":[72],"multiple":[73],"marketed":[74],"therapeutics,":[75],"including":[76],"celecoxib,":[77],"on":[78],"gram":[80],"scale.":[81],"The":[82],"SIL":[83],"products":[84],"also":[85,119],"exhibited":[86],"no":[87],"O/":[89],"16":[90],"back":[92],"exchange":[93],"under":[94],"extreme":[95],"conditions,":[96],"further":[97],"validating":[98],"utility":[100,141],"this":[102,143],"green":[103],"strategy":[104],"drug":[106],"both":[109],"in":[110,113],"vitro":[111],"vivo":[114],"use.":[115],"procedure":[117],"adapted":[120],"include":[122],"pharmaceutically":[123],"relevant":[124],"methyl":[125],"sulfones":[126],"by":[127],"13":[129],"CH":[130],",":[132],"affording":[133],"isotopic":[135],"enrichment,":[136],"thereby":[137],"illustrating":[138],"broad":[140],"methodology.":[144]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":2},{"year":2023,"cited_by_count":3},{"year":2022,"cited_by_count":3},{"year":2021,"cited_by_count":4},{"year":2020,"cited_by_count":2}],"updated_date":"2026-10-12T09:40:04.860316","created_date":"2025-10-10T00:00:00"}
