PMC:7571312 / 67187-68238 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/7571312","sourcedb":"PMC","sourceid":"7571312","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7571312","text":"(3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate\nA solution of tert-butyl ((1S)-3-bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (1.17 g, 3.2 mmol) in DMF (16 mL) was treated with 2,6-dichlorobenzoic acid (794 mg, 4.2 mmol) followed by cesium fluoride (1.18 g, 7.4 mmol). The resulting suspension was placed in a preheated oil bath at 65 °C for 2 h. The reaction was cooled to an ambient temperature, diluted with ethyl acetate (100 mL), washed once with water (40 mL) and with brine (40 mL), dried over MgSO4, filtered, and concentrated to give a crude yellow syrup. This material was purified by Biotage MPLC (25 M, 4.5% methanol/dichloromethane) to afford 1.19 mg (80%) of the title compound as an off-white glass. 1H NMR (400 MHz, DMSO-d6) δ 7.60 (m, 5H), 5.35 (s, 2H), 4.32 (m, 1H), 3.23 (m, 2H), 2.24 (m, 1H), 2.11 (m, 1H), 1.86 (m, 1H), 1.67 (m, 2H), 1.35 (s, 9H); MS (ESI+) for C20H24Cl2N2O6m/z 481.0 (M + Na)+; HRMS (ESI+) calcd for C20H24Cl2N2O6+H 481.0903, found 481.0890.","divisions":[{"label":"title","span":{"begin":0,"end":97}}],"tracks":[{"project":"LitCovid-PD-CLO","denotations":[{"id":"T529","span":{"begin":98,"end":99},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T530","span":{"begin":379,"end":380},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T531","span":{"begin":614,"end":615},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T532","span":{"begin":940,"end":942},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"}],"attributes":[{"subj":"T529","pred":"source","obj":"LitCovid-PD-CLO"},{"subj":"T530","pred":"source","obj":"LitCovid-PD-CLO"},{"subj":"T531","pred":"source","obj":"LitCovid-PD-CLO"},{"subj":"T532","pred":"source","obj":"LitCovid-PD-CLO"}]},{"project":"LitCovid-PD-CHEBI","denotations":[{"id":"T680","span":{"begin":29,"end":34},"obj":"Chemical"},{"id":"T681","span":{"begin":38,"end":41},"obj":"Chemical"},{"id":"T28223","span":{"begin":71,"end":76},"obj":"Chemical"},{"id":"T96207","span":{"begin":100,"end":108},"obj":"Chemical"},{"id":"T684","span":{"begin":112,"end":122},"obj":"Chemical"},{"id":"T8989","span":{"begin":117,"end":122},"obj":"Chemical"},{"id":"T686","span":{"begin":131,"end":136},"obj":"Chemical"},{"id":"T45200","span":{"begin":139,"end":142},"obj":"Chemical"},{"id":"T8478","span":{"begin":173,"end":179},"obj":"Chemical"},{"id":"T36282","span":{"begin":180,"end":186},"obj":"Chemical"},{"id":"T83154","span":{"begin":187,"end":196},"obj":"Chemical"},{"id":"T693","span":{"begin":219,"end":222},"obj":"Chemical"},{"id":"T46336","span":{"begin":248,"end":272},"obj":"Chemical"},{"id":"T695","span":{"begin":268,"end":272},"obj":"Chemical"},{"id":"T75958","span":{"begin":304,"end":310},"obj":"Chemical"},{"id":"T97736","span":{"begin":311,"end":319},"obj":"Chemical"},{"id":"T90033","span":{"begin":482,"end":495},"obj":"Chemical"},{"id":"T15643","span":{"begin":482,"end":487},"obj":"Chemical"},{"id":"T94319","span":{"begin":488,"end":495},"obj":"Chemical"},{"id":"T39328","span":{"begin":523,"end":528},"obj":"Chemical"},{"id":"T81342","span":{"begin":572,"end":577},"obj":"Chemical"},{"id":"T22666","span":{"begin":691,"end":699},"obj":"Chemical"},{"id":"T74066","span":{"begin":700,"end":715},"obj":"Chemical"},{"id":"T31384","span":{"begin":786,"end":788},"obj":"Chemical"},{"id":"T85312","span":{"begin":803,"end":807},"obj":"Chemical"},{"id":"T67067","span":{"begin":851,"end":853},"obj":"Chemical"},{"id":"T72314","span":{"begin":879,"end":881},"obj":"Chemical"},{"id":"T711","span":{"begin":893,"end":895},"obj":"Chemical"},{"id":"T90477","span":{"begin":907,"end":909},"obj":"Chemical"},{"id":"T98218","span":{"begin":940,"end":942},"obj":"Chemical"},{"id":"T65368","span":{"begin":982,"end":984},"obj":"Chemical"}],"attributes":[{"id":"A64387","pred":"chebi_id","subj":"T680","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A15771","pred":"chebi_id","subj":"T681","obj":"http://purl.obolibrary.org/obo/CHEBI_46629"},{"id":"A73080","pred":"chebi_id","subj":"T28223","obj":"http://purl.obolibrary.org/obo/CHEBI_41264"},{"id":"A68618","pred":"chebi_id","subj":"T96207","obj":"http://purl.obolibrary.org/obo/CHEBI_75958"},{"id":"A44687","pred":"chebi_id","subj":"T684","obj":"http://purl.obolibrary.org/obo/CHEBI_30355"},{"id":"A27864","pred":"chebi_id","subj":"T8989","obj":"http://purl.obolibrary.org/obo/CHEBI_41264"},{"id":"A94295","pred":"chebi_id","subj":"T686","obj":"http://purl.obolibrary.org/obo/CHEBI_22927"},{"id":"A6219","pred":"chebi_id","subj":"T686","obj":"http://purl.obolibrary.org/obo/CHEBI_47265"},{"id":"A49691","pred":"chebi_id","subj":"T45200","obj":"http://purl.obolibrary.org/obo/CHEBI_46629"},{"id":"A91470","pred":"chebi_id","subj":"T8478","obj":"http://purl.obolibrary.org/obo/CHEBI_32875"},{"id":"A51178","pred":"chebi_id","subj":"T8478","obj":"http://purl.obolibrary.org/obo/CHEBI_29309"},{"id":"A55669","pred":"chebi_id","subj":"T36282","obj":"http://purl.obolibrary.org/obo/CHEBI_26308"},{"id":"A18863","pred":"chebi_id","subj":"T83154","obj":"http://purl.obolibrary.org/obo/CHEBI_13941"},{"id":"A26946","pred":"chebi_id","subj":"T693","obj":"http://purl.obolibrary.org/obo/CHEBI_17741"},{"id":"A11206","pred":"chebi_id","subj":"T46336","obj":"http://purl.obolibrary.org/obo/CHEBI_48623"},{"id":"A34482","pred":"chebi_id","subj":"T695","obj":"http://purl.obolibrary.org/obo/CHEBI_37527"},{"id":"A59493","pred":"chebi_id","subj":"T75958","obj":"http://purl.obolibrary.org/obo/CHEBI_30514"},{"id":"A89499","pred":"chebi_id","subj":"T97736","obj":"http://purl.obolibrary.org/obo/CHEBI_17051"},{"id":"A92196","pred":"chebi_id","subj":"T90033","obj":"http://purl.obolibrary.org/obo/CHEBI_27750"},{"id":"A24845","pred":"chebi_id","subj":"T15643","obj":"http://purl.obolibrary.org/obo/CHEBI_37807"},{"id":"A61963","pred":"chebi_id","subj":"T15643","obj":"http://purl.obolibrary.org/obo/CHEBI_62801"},{"id":"A27773","pred":"chebi_id","subj":"T94319","obj":"http://purl.obolibrary.org/obo/CHEBI_30089"},{"id":"A2641","pred":"chebi_id","subj":"T94319","obj":"http://purl.obolibrary.org/obo/CHEBI_47622"},{"id":"A63389","pred":"chebi_id","subj":"T39328","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A35156","pred":"chebi_id","subj":"T81342","obj":"http://purl.obolibrary.org/obo/CHEBI_32599"},{"id":"A88811","pred":"chebi_id","subj":"T22666","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A95255","pred":"chebi_id","subj":"T74066","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A2856","pred":"chebi_id","subj":"T31384","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A88320","pred":"chebi_id","subj":"T85312","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A48932","pred":"chebi_id","subj":"T67067","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A83179","pred":"chebi_id","subj":"T72314","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A35677","pred":"chebi_id","subj":"T711","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A21743","pred":"chebi_id","subj":"T90477","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A9802","pred":"chebi_id","subj":"T98218","obj":"http://purl.obolibrary.org/obo/CHEBI_73613"},{"id":"A78875","pred":"chebi_id","subj":"T65368","obj":"http://purl.obolibrary.org/obo/CHEBI_26708"},{"subj":"T680","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T681","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T28223","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T96207","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T684","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T8989","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T686","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T45200","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T8478","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T36282","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T83154","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T693","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T46336","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T695","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T75958","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T97736","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T90033","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T15643","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T94319","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T39328","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T81342","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T22666","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T74066","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T31384","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T85312","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T67067","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T72314","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T711","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T90477","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T98218","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T65368","pred":"source","obj":"LitCovid-PD-CHEBI"}]},{"project":"LitCovid-sentences","denotations":[{"id":"T414","span":{"begin":0,"end":97},"obj":"Sentence"},{"id":"T415","span":{"begin":98,"end":339},"obj":"Sentence"},{"id":"T416","span":{"begin":340,"end":417},"obj":"Sentence"},{"id":"T417","span":{"begin":418,"end":635},"obj":"Sentence"},{"id":"T418","span":{"begin":636,"end":785},"obj":"Sentence"},{"id":"T419","span":{"begin":786,"end":1051},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"attributes":[{"subj":"T414","pred":"source","obj":"LitCovid-sentences"},{"subj":"T415","pred":"source","obj":"LitCovid-sentences"},{"subj":"T416","pred":"source","obj":"LitCovid-sentences"},{"subj":"T417","pred":"source","obj":"LitCovid-sentences"},{"subj":"T418","pred":"source","obj":"LitCovid-sentences"},{"subj":"T419","pred":"source","obj":"LitCovid-sentences"}]},{"project":"LitCovid-PubTator","denotations":[{"id":"1451","span":{"begin":0,"end":97},"obj":"Chemical"},{"id":"1464","span":{"begin":112,"end":196},"obj":"Chemical"},{"id":"1465","span":{"begin":219,"end":222},"obj":"Chemical"},{"id":"1466","span":{"begin":248,"end":272},"obj":"Chemical"},{"id":"1467","span":{"begin":304,"end":319},"obj":"Chemical"},{"id":"1468","span":{"begin":391,"end":394},"obj":"Chemical"},{"id":"1469","span":{"begin":482,"end":495},"obj":"Chemical"},{"id":"1470","span":{"begin":523,"end":528},"obj":"Chemical"},{"id":"1471","span":{"begin":546,"end":551},"obj":"Chemical"},{"id":"1472","span":{"begin":572,"end":577},"obj":"Chemical"},{"id":"1473","span":{"begin":691,"end":699},"obj":"Chemical"},{"id":"1474","span":{"begin":700,"end":715},"obj":"Chemical"},{"id":"1475","span":{"begin":988,"end":992},"obj":"Disease"}],"attributes":[{"id":"A1465","pred":"tao:has_database_id","subj":"1465","obj":"MESH:D004126"},{"id":"A1467","pred":"tao:has_database_id","subj":"1467","obj":"MESH:C027754"},{"id":"A1468","pred":"tao:has_database_id","subj":"1468","obj":"MESH:D009821"},{"id":"A1469","pred":"tao:has_database_id","subj":"1469","obj":"MESH:C007650"},{"id":"A1470","pred":"tao:has_database_id","subj":"1470","obj":"MESH:D014867"},{"id":"A1471","pred":"tao:has_database_id","subj":"1471","obj":"MESH:C017082"},{"id":"A1472","pred":"tao:has_database_id","subj":"1472","obj":"MESH:D008278"},{"id":"A1473","pred":"tao:has_database_id","subj":"1473","obj":"MESH:D000432"},{"id":"A1474","pred":"tao:has_database_id","subj":"1474","obj":"MESH:D008752"},{"subj":"1451","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1464","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1465","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1466","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1467","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1468","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1469","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1470","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1471","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1472","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1473","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1474","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1475","pred":"source","obj":"LitCovid-PubTator"}],"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_"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"LitCovid-PD-CLO","color":"#ec93db","default":true},{"id":"LitCovid-PD-CHEBI","color":"#93ece3"},{"id":"LitCovid-sentences","color":"#ecc993"},{"id":"LitCovid-PubTator","color":"#af93ec"}]}]}}