PMC:7571312 / 70876-71995 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T552","span":{"begin":419,"end":420},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T553","span":{"begin":571,"end":572},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T554","span":{"begin":895,"end":897},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T555","span":{"begin":933,"end":938},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"(3S)-3-[(N-Acetyl-l-leucyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (30)\nFollowing the procedure described for the preparation of N2-acetyl-N1-[(1S)-1-(chloroacetyl)-4-(dimethylamino)-4-oxobutyl]-N2-methyl-l-leucinamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a pale yellow oil. This material was purified by Biotage MPLC (25 M, 3.5–4.5% methanol/dichloromethane) to afford 161 mg (78%) of the title compound as a white foam. 1H NMR (DMSO-d6) δ 8.56 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.65–7.53 (m, 4H), 5.17 (d, J = 16 Hz, 1H), 5.10 (d, J = 16 Hz, 1H), 4.44 (m, 1H), 4.25 (m, 1H), 3.12 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (s, 3H), 1.63 (m, 3H), 1.45 (m, 2H), 0.90 (d, J = 8 Hz, 3H), 0.85 (d, J = 8 Hz, 3H); MS (ESI+) for C23H29Cl2N3O6m/z 514.0 (M + H)+; anal. calcd for C23H29Cl2N3O6·0.25 H2O·0.1 EtOAc: C, 53.26; H, 5.79; N, 7.96. Found: C, 53.27; H, 5.82; N, 7.84. HRMS (ESI+) calcd for C23H29Cl2N3O6+H1 514.1506, found 514.1508."}

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2,6-Dichlorobenzoate (30)\nFollowing the procedure described for the preparation of N2-acetyl-N1-[(1S)-1-(chloroacetyl)-4-(dimethylamino)-4-oxobutyl]-N2-methyl-l-leucinamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a pale yellow oil. This material was purified by Biotage MPLC (25 M, 3.5–4.5% methanol/dichloromethane) to afford 161 mg (78%) of the title compound as a white foam. 1H NMR (DMSO-d6) δ 8.56 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.65–7.53 (m, 4H), 5.17 (d, J = 16 Hz, 1H), 5.10 (d, J = 16 Hz, 1H), 4.44 (m, 1H), 4.25 (m, 1H), 3.12 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (s, 3H), 1.63 (m, 3H), 1.45 (m, 2H), 0.90 (d, J = 8 Hz, 3H), 0.85 (d, J = 8 Hz, 3H); MS (ESI+) for C23H29Cl2N3O6m/z 514.0 (M + H)+; anal. calcd for C23H29Cl2N3O6·0.25 H2O·0.1 EtOAc: C, 53.26; H, 5.79; N, 7.96. Found: C, 53.27; H, 5.82; N, 7.84. HRMS (ESI+) calcd for C23H29Cl2N3O6+H1 514.1506, found 514.1508."}

{"project":"LitCovid-sentences","denotations":[{"id":"T436","span":{"begin":0,"end":100},"obj":"Sentence"},{"id":"T437","span":{"begin":101,"end":437},"obj":"Sentence"},{"id":"T438","span":{"begin":438,"end":584},"obj":"Sentence"},{"id":"T439","span":{"begin":585,"end":1019},"obj":"Sentence"},{"id":"T440","span":{"begin":1020,"end":1054},"obj":"Sentence"},{"id":"T441","span":{"begin":1055,"end":1119},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"(3S)-3-[(N-Acetyl-l-leucyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (30)\nFollowing the procedure described for the preparation of N2-acetyl-N1-[(1S)-1-(chloroacetyl)-4-(dimethylamino)-4-oxobutyl]-N2-methyl-l-leucinamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a pale yellow oil. This material was purified by Biotage MPLC (25 M, 3.5–4.5% methanol/dichloromethane) to afford 161 mg (78%) of the title compound as a white foam. 1H NMR (DMSO-d6) δ 8.56 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.65–7.53 (m, 4H), 5.17 (d, J = 16 Hz, 1H), 5.10 (d, J = 16 Hz, 1H), 4.44 (m, 1H), 4.25 (m, 1H), 3.12 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (s, 3H), 1.63 (m, 3H), 1.45 (m, 2H), 0.90 (d, J = 8 Hz, 3H), 0.85 (d, J = 8 Hz, 3H); MS (ESI+) for C23H29Cl2N3O6m/z 514.0 (M + H)+; anal. calcd for C23H29Cl2N3O6·0.25 H2O·0.1 EtOAc: C, 53.26; H, 5.79; N, 7.96. Found: C, 53.27; H, 5.82; N, 7.84. HRMS (ESI+) calcd for C23H29Cl2N3O6+H1 514.1506, found 514.1508."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1531","span":{"begin":0,"end":95},"obj":"Chemical"},{"id":"1543","span":{"begin":497,"end":505},"obj":"Chemical"},{"id":"1544","span":{"begin":506,"end":521},"obj":"Chemical"},{"id":"1545","span":{"begin":958,"end":971},"obj":"Chemical"},{"id":"1546","span":{"begin":977,"end":980},"obj":"Chemical"},{"id":"1547","span":{"begin":985,"end":990},"obj":"Chemical"},{"id":"1548","span":{"begin":992,"end":993},"obj":"Chemical"},{"id":"1549","span":{"begin":1011,"end":1012},"obj":"Chemical"},{"id":"1550","span":{"begin":1027,"end":1028},"obj":"Chemical"},{"id":"1551","span":{"begin":1046,"end":1047},"obj":"Chemical"},{"id":"1552","span":{"begin":1077,"end":1090},"obj":"Chemical"},{"id":"1553","span":{"begin":1055,"end":1059},"obj":"Disease"}],"attributes":[{"id":"A1543","pred":"tao:has_database_id","subj":"1543","obj":"MESH:D000432"},{"id":"A1544","pred":"tao:has_database_id","subj":"1544","obj":"MESH:D008752"},{"id":"A1548","pred":"tao:has_database_id","subj":"1548","obj":"MESH:D002244"},{"id":"A1549","pred":"tao:has_database_id","subj":"1549","obj":"MESH:D009584"},{"id":"A1550","pred":"tao:has_database_id","subj":"1550","obj":"MESH:D002244"},{"id":"A1551","pred":"tao:has_database_id","subj":"1551","obj":"MESH:D009584"}],"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":"(3S)-3-[(N-Acetyl-l-leucyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate (30)\nFollowing the procedure described for the preparation of N2-acetyl-N1-[(1S)-1-(chloroacetyl)-4-(dimethylamino)-4-oxobutyl]-N2-methyl-l-leucinamide but substituting (3S)-3-{[N-(tert-butoxycarbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate and making noncritical variations provided a pale yellow oil. This material was purified by Biotage MPLC (25 M, 3.5–4.5% methanol/dichloromethane) to afford 161 mg (78%) of the title compound as a white foam. 1H NMR (DMSO-d6) δ 8.56 (d, J = 8 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.65–7.53 (m, 4H), 5.17 (d, J = 16 Hz, 1H), 5.10 (d, J = 16 Hz, 1H), 4.44 (m, 1H), 4.25 (m, 1H), 3.12 (m, 2H), 2.25 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (s, 3H), 1.63 (m, 3H), 1.45 (m, 2H), 0.90 (d, J = 8 Hz, 3H), 0.85 (d, J = 8 Hz, 3H); MS (ESI+) for C23H29Cl2N3O6m/z 514.0 (M + H)+; anal. calcd for C23H29Cl2N3O6·0.25 H2O·0.1 EtOAc: C, 53.26; H, 5.79; N, 7.96. Found: C, 53.27; H, 5.82; N, 7.84. HRMS (ESI+) calcd for C23H29Cl2N3O6+H1 514.1506, found 514.1508."}