PMC:7571312 / 55855-56885 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T487","span":{"begin":249,"end":250},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T488","span":{"begin":885,"end":887},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T489","span":{"begin":920,"end":925},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyanobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 159 mg (75%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.09–8.14 (m, 2H), 7.99–8.05 (m, 2H), 7.66 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.17 (d, J = 2.8 Hz, 1H), 5.11–5.27 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+. Anal. calcd for C32H35N5O7·0.90 H2O: C, 62.21; H, 6.00; N, 11.33. Found: C, 62.23; H, 6.06; N, 11.58."}

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the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyanobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 159 mg (75%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.09–8.14 (m, 2H), 7.99–8.05 (m, 2H), 7.66 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.17 (d, J = 2.8 Hz, 1H), 5.11–5.27 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+. Anal. calcd for C32H35N5O7·0.90 H2O: C, 62.21; H, 6.00; N, 11.33. Found: C, 62.23; H, 6.06; N, 11.58."}

{"project":"LitCovid-sentences","denotations":[{"id":"T360","span":{"begin":0,"end":265},"obj":"Sentence"},{"id":"T361","span":{"begin":266,"end":396},"obj":"Sentence"},{"id":"T362","span":{"begin":397,"end":928},"obj":"Sentence"},{"id":"T363","span":{"begin":929,"end":994},"obj":"Sentence"},{"id":"T364","span":{"begin":995,"end":1030},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyanobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 159 mg (75%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.09–8.14 (m, 2H), 7.99–8.05 (m, 2H), 7.66 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.17 (d, J = 2.8 Hz, 1H), 5.11–5.27 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+. Anal. calcd for C32H35N5O7·0.90 H2O: C, 62.21; H, 6.00; N, 11.33. Found: C, 62.23; H, 6.06; N, 11.58."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1257","span":{"begin":186,"end":205},"obj":"Chemical"},{"id":"1258","span":{"begin":325,"end":333},"obj":"Chemical"},{"id":"1259","span":{"begin":334,"end":349},"obj":"Chemical"},{"id":"1260","span":{"begin":945,"end":955},"obj":"Chemical"},{"id":"1261","span":{"begin":961,"end":964},"obj":"Chemical"},{"id":"1262","span":{"begin":966,"end":967},"obj":"Chemical"},{"id":"1263","span":{"begin":985,"end":986},"obj":"Chemical"},{"id":"1264","span":{"begin":1002,"end":1003},"obj":"Chemical"},{"id":"1265","span":{"begin":1021,"end":1022},"obj":"Chemical"}],"attributes":[{"id":"A1257","pred":"tao:has_database_id","subj":"1257","obj":"MESH:C097383"},{"id":"A1258","pred":"tao:has_database_id","subj":"1258","obj":"MESH:D000432"},{"id":"A1259","pred":"tao:has_database_id","subj":"1259","obj":"MESH:D008752"},{"id":"A1262","pred":"tao:has_database_id","subj":"1262","obj":"MESH:D002244"},{"id":"A1263","pred":"tao:has_database_id","subj":"1263","obj":"MESH:D009584"},{"id":"A1264","pred":"tao:has_database_id","subj":"1264","obj":"MESH:D002244"},{"id":"A1265","pred":"tao:has_database_id","subj":"1265","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":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-cyanobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 159 mg (75%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 2.0 Hz, 1H), 8.64 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 8.09–8.14 (m, 2H), 7.99–8.05 (m, 2H), 7.66 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.17 (d, J = 2.8 Hz, 1H), 5.11–5.27 (m, 1H), 4.44–4.53 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.28–2.38 (m, 1H), 2.07–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+. Anal. calcd for C32H35N5O7·0.90 H2O: C, 62.21; H, 6.00; N, 11.33. Found: C, 62.23; H, 6.06; N, 11.58."}