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PMC:7571312 / 97245-98669 JSONTXT

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LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T95 1033-1036 Body_part denotes gum http://purl.org/sig/ont/fma/fma59762

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T667 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T668 792-800 http://purl.obolibrary.org/obo/OBI_0100026 denotes organics
T669 792-800 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organics
T670 1020-1021 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T671 1033-1036 http://www.ebi.ac.uk/efo/EFO_0001925 denotes gum

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T74760 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T79325 17-27 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T98057 22-27 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T22604 50-53 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T25590 84-90 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T71034 91-97 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T7146 98-107 Chemical denotes carbamate http://purl.obolibrary.org/obo/CHEBI_13941
T64367 131-138 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T97507 160-177 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T47345 173-177 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T86277 178-185 Chemical denotes dioxane http://purl.obolibrary.org/obo/CHEBI_46923
T33926 202-210 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T50802 277-285 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T66031 325-332 Chemical denotes toluene http://purl.obolibrary.org/obo/CHEBI_17578
T70328 385-398 Chemical denotes hydrochloride http://purl.obolibrary.org/obo/CHEBI_36807
T42778 399-403 Chemical denotes salt http://purl.obolibrary.org/obo/CHEBI_24866|http://purl.obolibrary.org/obo/CHEBI_26710
T49099 419-422 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T36941 439-447 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T53628 483-486 Chemical denotes Boc http://purl.obolibrary.org/obo/CHEBI_48502
T38411 702-707 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T50847 725-732 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T50559 752-765 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T93140 760-765 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T31300 817-822 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T91535 842-850 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T36747 963-971 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T28856 972-987 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T50448 1118-1120 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38103 1135-1140 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1914 1165-1167 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37713 1198-1200 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24526 1224-1226 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T44060 1238-1240 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29984 1265-1267 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68855 1292-1294 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T551 0-374 Sentence denotes To a solution of tert-butyl ((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)carbamate (200 mg, 0.53 mmol) in dioxane (5 mL) was added 4 M hydrochloric acid/dioxane (5 mL), and the solution was stirred at an ambient temperature for 4 h before removing the solvents in vacuo, azeotroping the residue with toluene (2 × 10 mL), and drying in vacuo for 1 h.
T552 375-656 Sentence denotes The crude hydrochloride salt was taken into DMF (3 mL), and the solution was cooled to 0 °C before adding N-Boc-cyclohexylalanine-OH (139 mg, 0.53 mmol), collidine (156 μL, 1.22 mmol), and HATU (194 mg, 0.53 mmol) in order, and the resulting suspension was stirred at 0 °C for 5 h.
T553 657-778 Sentence denotes The reaction was quenched by the addition of water (30 mL), and the mixture was extracted with diethyl ether (3 × 75 mL).
T554 779-1050 Sentence denotes The combined organics were dried over MgSO4, filtered, and the solvents were removed in vacuo to yield the crude product, which was purified by flash chromatography, eluting with 1–3% methanol/dichloromethane to afford the title compound as a pale brown gum, 205 mg, 76%.
T555 1051-1117 Sentence denotes The product was contaminated with ∼20% of another diastereoisomer.
T556 1118-1424 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J = 5.6 Hz, 1H), 7.26–7.42 (m, 5H), 5.93 (s, 1H), 4.94 (d, J = 7.6 Hz, 1H), 4.72 (m, 1H), 4.60 (d, J = 11.6 Hz, 1H), 4.55 (d, J = 11.6 Hz, 1H), 4.14–4.34 (m, 3H), 3.27 (m, 2H), 2.23–2.51 (m, 3H), 1.56–2.05 (m, 9H), 1.33–1.48 (m, 9H), 1.05–1.29 (m, 4H), 0.80–1.03 (m, 2H).

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1854 483-486 Gene denotes Boc Gene:91653
1855 1027-1036 Species denotes brown gum Tax:338536
1856 702-707 Chemical denotes water MESH:D014867
1857 817-822 Chemical denotes MgSO4 MESH:D008278
1858 963-971 Chemical denotes methanol MESH:D000432
1859 972-987 Chemical denotes dichloromethane MESH:D008752