PMC:7571312 / 11027-12006 JSON TXT

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LitCovid-PD-FMA-UBERON

{"project":"LitCovid-PD-FMA-UBERON","denotations":[{"id":"T53161","span":{"begin":63,"end":73},"obj":"Body_part"}],"attributes":[{"id":"A88520","pred":"fma_id","subj":"T53161","obj":"http://purl.org/sig/ont/fma/fma82739"}],"text":"Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield. Acid 6 was treated with isobutylchloroformate and triethylamine, and the resulting mixed anhydride was reacted with diazomethane34 to provide high isolated yields of 7. Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10. Alternatively, the N-Boc-protected bromomethylketone was prepared by treatment of 7 with stoichiometric quantities of 48% HBr in dichloromethane to provide 11. Another preparation of CMK intermediates that avoids the use of diazomethane was accomplished by the reaction of 5 with excess LDA and chloroiodomethane to afford 8 in moderate yields. A direct approach to oxymethylketone intermediate 9 was achieved by conversion of acid 6 to the corresponding Weinreb amide followed by treatment with the Grignard generated from benzyl chloromethyl ether.35"}

LitCovid-PD-CLO

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T19787","span":{"begin":405,"end":408},"obj":"http://purl.obolibrary.org/obo/CLO_0002526"},{"id":"T8586","span":{"begin":545,"end":547},"obj":"http://purl.obolibrary.org/obo/CLO_0001382"},{"id":"T41909","span":{"begin":583,"end":585},"obj":"http://purl.obolibrary.org/obo/CLO_0053733"},{"id":"T84353","span":{"begin":610,"end":613},"obj":"http://purl.obolibrary.org/obo/CLO_0002526"},{"id":"T64722","span":{"begin":772,"end":773},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T21026","span":{"begin":977,"end":979},"obj":"http://purl.obolibrary.org/obo/CLO_0001000"}],"text":"Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield. Acid 6 was treated with isobutylchloroformate and triethylamine, and the resulting mixed anhydride was reacted with diazomethane34 to provide high isolated yields of 7. Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10. Alternatively, the N-Boc-protected bromomethylketone was prepared by treatment of 7 with stoichiometric quantities of 48% HBr in dichloromethane to provide 11. Another preparation of CMK intermediates that avoids the use of diazomethane was accomplished by the reaction of 5 with excess LDA and chloroiodomethane to afford 8 in moderate yields. A direct approach to oxymethylketone intermediate 9 was achieved by conversion of acid 6 to the corresponding Weinreb amide followed by treatment with the Grignard generated from benzyl chloromethyl ether.35"}

LitCovid-PD-CHEBI

LitCovid-sentences

{"project":"LitCovid-sentences","denotations":[{"id":"T55","span":{"begin":0,"end":105},"obj":"Sentence"},{"id":"T56","span":{"begin":106,"end":274},"obj":"Sentence"},{"id":"T57","span":{"begin":275,"end":426},"obj":"Sentence"},{"id":"T58","span":{"begin":427,"end":586},"obj":"Sentence"},{"id":"T59","span":{"begin":587,"end":771},"obj":"Sentence"},{"id":"T60","span":{"begin":772,"end":979},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield. Acid 6 was treated with isobutylchloroformate and triethylamine, and the resulting mixed anhydride was reacted with diazomethane34 to provide high isolated yields of 7. Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10. Alternatively, the N-Boc-protected bromomethylketone was prepared by treatment of 7 with stoichiometric quantities of 48% HBr in dichloromethane to provide 11. Another preparation of CMK intermediates that avoids the use of diazomethane was accomplished by the reaction of 5 with excess LDA and chloroiodomethane to afford 8 in moderate yields. A direct approach to oxymethylketone intermediate 9 was achieved by conversion of acid 6 to the corresponding Weinreb amide followed by treatment with the Grignard generated from benzyl chloromethyl ether.35"}

LitCovid-PubTator

{"project":"LitCovid-PubTator","denotations":[{"id":"279","span":{"begin":448,"end":451},"obj":"Gene"},{"id":"280","span":{"begin":18,"end":29},"obj":"Chemical"},{"id":"281","span":{"begin":130,"end":151},"obj":"Chemical"},{"id":"282","span":{"begin":156,"end":169},"obj":"Chemical"},{"id":"283","span":{"begin":222,"end":234},"obj":"Chemical"},{"id":"284","span":{"begin":275,"end":286},"obj":"Chemical"},{"id":"285","span":{"begin":306,"end":323},"obj":"Chemical"},{"id":"286","span":{"begin":341,"end":349},"obj":"Chemical"},{"id":"287","span":{"begin":385,"end":403},"obj":"Chemical"},{"id":"288","span":{"begin":405,"end":408},"obj":"Chemical"},{"id":"289","span":{"begin":556,"end":571},"obj":"Chemical"},{"id":"290","span":{"begin":651,"end":663},"obj":"Chemical"},{"id":"291","span":{"begin":714,"end":717},"obj":"Chemical"},{"id":"292","span":{"begin":722,"end":739},"obj":"Chemical"},{"id":"293","span":{"begin":793,"end":808},"obj":"Chemical"},{"id":"294","span":{"begin":882,"end":895},"obj":"Chemical"},{"id":"295","span":{"begin":951,"end":976},"obj":"Chemical"}],"attributes":[{"id":"A279","pred":"tao:has_database_id","subj":"279","obj":"Gene:91653"},{"id":"A281","pred":"tao:has_database_id","subj":"281","obj":"MESH:C039311"},{"id":"A282","pred":"tao:has_database_id","subj":"282","obj":"MESH:C016162"},{"id":"A283","pred":"tao:has_database_id","subj":"283","obj":"MESH:D003978"},{"id":"A285","pred":"tao:has_database_id","subj":"285","obj":"MESH:D006851"},{"id":"A286","pred":"tao:has_database_id","subj":"286","obj":"MESH:D009584"},{"id":"A289","pred":"tao:has_database_id","subj":"289","obj":"MESH:D008752"},{"id":"A290","pred":"tao:has_database_id","subj":"290","obj":"MESH:D003978"},{"id":"A291","pred":"tao:has_database_id","subj":"291","obj":"MESH:C007442"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"Saponification of amino ester 5(33) afforded the corresponding amino acid 6 in nearly quantitative yield. Acid 6 was treated with isobutylchloroformate and triethylamine, and the resulting mixed anhydride was reacted with diazomethane34 to provide high isolated yields of 7. Diazoketone 7 was treated with hydrochloric acid for simultaneous nitrogen deprotection and conversion to the chloromethylketone (CMK) intermediate 10. Alternatively, the N-Boc-protected bromomethylketone was prepared by treatment of 7 with stoichiometric quantities of 48% HBr in dichloromethane to provide 11. Another preparation of CMK intermediates that avoids the use of diazomethane was accomplished by the reaction of 5 with excess LDA and chloroiodomethane to afford 8 in moderate yields. A direct approach to oxymethylketone intermediate 9 was achieved by conversion of acid 6 to the corresponding Weinreb amide followed by treatment with the Grignard generated from benzyl chloromethyl ether.35"}