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PMC:7571312 / 40032-41712 JSONTXT

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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T89 98-102 Body_part denotes neck http://purl.org/sig/ont/fma/fma7155
T90 257-266 Body_part denotes alaninate http://purl.org/sig/ont/fma/fma82749

LitCovid-PD-UBERON

Id Subject Object Predicate Lexical cue uberon_id
T14 98-102 Body_part denotes neck http://purl.obolibrary.org/obo/UBERON_0000974

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T400 90-91 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T401 98-102 http://www.ebi.ac.uk/efo/EFO_0000967 denotes neck
T402 135-136 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T403 271-276 http://purl.obolibrary.org/obo/CLO_0003431 denotes g, 35
T404 456-457 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T405 502-503 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T406 647-648 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T407 695-696 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T408 948-956 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T409 948-956 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T410 1130-1131 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T411 1299-1300 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T412 1537-1539 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T413 1545-1547 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T659 28-31 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T660 62-68 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T662 69-75 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T663 76-85 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T664 137-145 Chemical denotes nitrogen http://purl.obolibrary.org/obo/CHEBI_25555
T665 194-200 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T667 204-223 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T668 257-266 Chemical denotes alaninate http://purl.obolibrary.org/obo/CHEBI_32439
T669 284-287 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T672 349-357 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T673 414-417 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T676 429-440 Chemical denotes cyclohexane http://purl.obolibrary.org/obo/CHEBI_29005
T677 649-656 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T678 660-664 Chemical denotes AcOH http://purl.obolibrary.org/obo/CHEBI_15366
T679 677-680 Chemical denotes THF http://purl.obolibrary.org/obo/CHEBI_15635|http://purl.obolibrary.org/obo/CHEBI_20506|http://purl.obolibrary.org/obo/CHEBI_26911
T682 916-929 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T683 916-921 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T685 922-929 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T687 974-979 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T688 996-1002 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T689 1044-1049 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T690 1069-1077 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T691 1198-1211 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T692 1198-1203 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T694 1204-1211 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T696 1253-1266 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T697 1261-1266 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T698 1332-1334 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T699 1349-1353 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T700 1369-1371 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T701 1395-1397 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T702 1428-1430 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T703 1461-1463 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T704 1480-1482 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T705 1499-1501 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T706 1537-1539 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T707 1545-1547 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T708 1582-1584 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T275 0-89 Sentence denotes tert-Butyl ((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (8)
T276 90-379 Sentence denotes A three-neck flame-dried flask equipped with a nitrogen inlet and internal thermometer was charged with methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate (10 g, 35 mmol), THF (200 mL), and chloroiodomethane (10.2 mL, 140 mmol), and the solution was cooled to −77 °C.
T277 380-555 Sentence denotes LDA (140 mL, 210 mmol, 1.5 M mono-THF complex in cyclohexane) was added via a pressure-equalizing dropping funnel at such a rate to keep the internal temperature below −70 °C.
T278 556-774 Sentence denotes After complete addition, the reaction was stirred for an additional hour and quenched with a mixture of AcOH (33 mL) and THF (200 mL) with a rate of addition regulated to maintain the internal temperature below −65 °C.
T279 775-885 Sentence denotes After complete addition, the dark suspension was stirred for 10 min and then warmed to an ambient temperature.
T280 886-995 Sentence denotes The reaction was diluted with ethyl acetate (500 mL), and the organics were washed with water (250 mL), satd.
T281 996-1212 Sentence denotes NaHCO3 (250 mL), and brine (250 mL), dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product as a dark oil, which was purified by flash chromatography eluting with ethyl acetate.
T282 1213-1331 Sentence denotes The resulting solid was triturated with diethyl ether to afford the title compound as a pale yellow solid, 5.7 g, 54%.
T283 1332-1645 Sentence denotes 1H NMR (400 MHz, DMSO-d6) δ 7.88 (s, 1H), 7.75 (d, J = 7.6 Hz, 1H), 4.73–4.94 (m, 2H), 4.37 (m, 1H), 3.28–3.43 (m, 2H), 2.46 (m, 1H), 2.30–2.40 (m, 1H), 2.02–2.14 (m, 1H), 1.77–1.95 (m, 2H), 1.60 (s, 9H); MS (API-ES+) for C13H21N2O4Cl m/z 327.1 (M + Na)+; anal. calcd for C13H21ClN2O4: C, 51.23; H, 6.95; N, 9.19.
T284 1646-1680 Sentence denotes Found: C, 51.03; H, 6.93; N, 9.03.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
989 0-85 Chemical denotes tert-Butyl ((1S)-3-Chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate
1003 137-145 Chemical denotes nitrogen MESH:D009584
1004 916-929 Chemical denotes ethyl acetate MESH:C007650
1005 974-979 Chemical denotes water MESH:D014867
1006 996-1002 Chemical denotes NaHCO3 MESH:D017693
1007 1017-1022 Chemical denotes brine MESH:C017082
1008 1044-1049 Chemical denotes MgSO4 MESH:D008278
1009 1198-1211 Chemical denotes ethyl acetate MESH:C007650
1010 1253-1266 Chemical denotes diethyl ether MESH:D004986
1011 1604-1616 Chemical denotes C13H21ClN2O4
1012 1618-1619 Chemical denotes C MESH:D002244
1013 1637-1638 Chemical denotes N MESH:D009584
1014 1653-1654 Chemical denotes C MESH:D002244
1015 1672-1673 Chemical denotes N MESH:D009584