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PMC:7571312 / 37079-38414 JSONTXT

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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T85 56-63 Body_part denotes alanine http://purl.org/sig/ont/fma/fma82749
T86 229-238 Body_part denotes alaninate http://purl.org/sig/ont/fma/fma82749

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T375 68-71 http://purl.obolibrary.org/obo/CLO_0001577 denotes A 3
T376 458-459 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T377 504-505 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T378 889-890 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T379 911-919 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T380 911-919 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T381 1010-1018 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T382 1010-1018 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T383 1119-1120 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T384 1291-1293 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T385 1327-1332 http://purl.obolibrary.org/obo/CLO_0007706 denotes M – H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T578 56-63 Chemical denotes alanine http://purl.obolibrary.org/obo/CHEBI_16449
T579 166-172 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T581 176-195 Chemical denotes tert-butoxycarbonyl http://purl.obolibrary.org/obo/CHEBI_48502
T582 229-238 Chemical denotes alaninate http://purl.obolibrary.org/obo/CHEBI_32439
T583 284-292 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T584 308-316 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T585 346-350 Chemical denotes NaCl http://purl.obolibrary.org/obo/CHEBI_26710
T586 357-361 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T587 379-384 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T588 395-403 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T589 574-582 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T590 642-659 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T591 655-659 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T592 729-737 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T593 777-790 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T594 777-782 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T596 783-790 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T598 830-847 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T599 843-847 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T600 862-869 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T601 965-978 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T602 965-970 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T604 971-978 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T606 1054-1059 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T607 1138-1140 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T608 1177-1179 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T609 1215-1217 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T610 1234-1236 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T611 1253-1255 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T612 1291-1293 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T255 0-67 Sentence denotes N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)
T256 68-356 Sentence denotes A 3 L multineck flask equipped with an overhead stirrer and internal thermometer was charged with methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate (compound 5)33 (205 g, 716 mmol) followed by methanol (1 L), and the solution was cooled to 0 °C using ice/NaCl bath.
T257 357-559 Sentence denotes NaOH (115 g in 950 mL water, 2.9 mol) solution was precooled to 0 °C and then added to the flask via a pressure-equalizing dropping funnel at such a rate to maintain the internal temperature below 5 °C.
T258 560-747 Sentence denotes The resulting solution was stirred at 0 °C for 1 h before neutralizing with conc. hydrochloric acid (keeping the internal temperature below 10 °C) and then removing the methanol in vacuo.
T259 748-933 Sentence denotes The residue was diluted with ethyl acetate (400 mL), acidified to pH 3 with conc. hydrochloric acid, and then the mixture was transferred to a sep funnel, and the organics were removed.
T260 934-1137 Sentence denotes The aqueous was extracted with ethyl acetate (2 × 400 mL), and the combined organics were washed with brine, dried over MgSO4, filtered, and concentrated to yield the title compound as a white foam, 95%.
T261 1138-1335 Sentence denotes 1H NMR (400 MHz, MeOD) δ 3.98–4.28 (m, 1H), 3.25–3.41 (m, 2H), 2.44–2.57 (m, 1H), 2.29–2.41 (m, 1H), 2.03–2.14 (m, 1H), 1.73–1.90 (m, 2H), 1.44 (s, 9H); MS (APCI−) for C12H20N2O5m/z 272.3 (M – H)−.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
923 0-63 Chemical denotes N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine
937 166-238 Chemical denotes methyl N-(tert-butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alaninate
938 284-292 Chemical denotes methanol MESH:D000432
939 342-345 Chemical denotes ice MESH:D007053
940 346-350 Chemical denotes NaCl MESH:D012965
941 357-361 Chemical denotes NaOH
942 379-384 Chemical denotes water MESH:D014867
943 642-659 Chemical denotes hydrochloric acid MESH:D006851
944 729-737 Chemical denotes methanol MESH:D000432
945 777-790 Chemical denotes ethyl acetate MESH:C007650
946 830-847 Chemical denotes hydrochloric acid MESH:D006851
947 965-978 Chemical denotes ethyl acetate MESH:C007650
948 1036-1041 Chemical denotes brine MESH:C017082
949 1054-1059 Chemical denotes MgSO4 MESH:D008278