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PMC:7571312 / 67187-68238 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T529 98-99 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T530 379-380 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T531 614-615 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T532 940-942 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T680 29-34 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T681 38-41 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T28223 71-76 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T96207 100-108 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T684 112-122 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T8989 117-122 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T686 131-136 Chemical denotes bromo http://purl.obolibrary.org/obo/CHEBI_22927|http://purl.obolibrary.org/obo/CHEBI_47265
T45200 139-142 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T8478 173-179 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T36282 180-186 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T83154 187-196 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T693 219-222 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T46336 248-272 Chemical denotes 2,6-dichlorobenzoic acid http://purl.obolibrary.org/obo/CHEBI_48623
T695 268-272 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T75958 304-310 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T97736 311-319 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T90033 482-495 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T15643 482-487 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T94319 488-495 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T39328 523-528 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T81342 572-577 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T22666 691-699 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T74066 700-715 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T31384 786-788 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85312 803-807 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T67067 851-853 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T72314 879-881 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T711 893-895 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T90477 907-909 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98218 940-942 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T65368 982-984 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T414 0-97 Sentence denotes (3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate
T415 98-339 Sentence denotes A 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).
T416 340-417 Sentence denotes The resulting suspension was placed in a preheated oil bath at 65 °C for 2 h.
T417 418-635 Sentence denotes 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.
T418 636-785 Sentence denotes 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.
T419 786-1051 Sentence denotes 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.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1451 0-97 Chemical denotes (3S)-3-[(tert-Butoxycarbonyl)amino]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-Dichlorobenzoate
1464 112-196 Chemical denotes tert-butyl ((1S)-3-bromo-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1465 219-222 Chemical denotes DMF MESH:D004126
1466 248-272 Chemical denotes 2,6-dichlorobenzoic acid
1467 304-319 Chemical denotes cesium fluoride MESH:C027754
1468 391-394 Chemical denotes oil MESH:D009821
1469 482-495 Chemical denotes ethyl acetate MESH:C007650
1470 523-528 Chemical denotes water MESH:D014867
1471 546-551 Chemical denotes brine MESH:C017082
1472 572-577 Chemical denotes MgSO4 MESH:D008278
1473 691-699 Chemical denotes methanol MESH:D000432
1474 700-715 Chemical denotes dichloromethane MESH:D008752
1475 988-992 Disease denotes HRMS