> top > docs > PMC:7571312 > spans > 91592-92783 > annotations

PMC:7571312 / 91592-92783 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T642 58-59 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T643 451-452 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T644 915-916 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T645 1145-1147 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T646 1153-1155 http://purl.obolibrary.org/obo/CLO_0053755 denotes ES

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T1714 33-39 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1716 60-68 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1717 72-78 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1719 82-114 Chemical denotes (9H-fluoren-9-ylmethoxy)carbonyl http://purl.obolibrary.org/obo/CHEBI_48605
T1720 106-114 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1721 118-124 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1723 163-166 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T1724 185-187 Chemical denotes KF http://purl.obolibrary.org/obo/CHEBI_73605
T1725 221-234 Chemical denotes triethylamine http://purl.obolibrary.org/obo/CHEBI_35026
T1726 261-286 Chemical denotes di-tert-butyl dicarbonate http://purl.obolibrary.org/obo/CHEBI_48500
T1727 264-274 Chemical denotes tert-butyl http://purl.obolibrary.org/obo/CHEBI_30355
T1728 269-274 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1729 308-315 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1730 426-433 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1731 471-473 Chemical denotes KF http://purl.obolibrary.org/obo/CHEBI_73605
T1732 541-548 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T1733 566-579 Chemical denotes diethyl ether http://purl.obolibrary.org/obo/CHEBI_35702
T1734 574-579 Chemical denotes ether http://purl.obolibrary.org/obo/CHEBI_25698
T1735 608-614 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T1736 632-649 Chemical denotes hydrochloric acid http://purl.obolibrary.org/obo/CHEBI_17883
T1737 645-649 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1738 663-669 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T1739 709-714 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1740 734-742 Chemical denotes solvents http://purl.obolibrary.org/obo/CHEBI_46787
T1741 860-875 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T1742 876-882 Chemical denotes hexane http://purl.obolibrary.org/obo/CHEBI_29021
T1743 941-943 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1744 958-963 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T1745 988-990 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1746 1007-1009 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1747 1040-1042 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1748 1145-1147 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1749 1153-1155 Chemical denotes ES http://purl.obolibrary.org/obo/CHEBI_73509
T1750 1186-1188 Chemical denotes Na http://purl.obolibrary.org/obo/CHEBI_26708

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T527 0-54 Sentence denotes Methyl N-(tert-Butoxycarbonyl)-5-methyl-l-norleucinate
T528 55-354 Sentence denotes To a solution of methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate (2.18 g, 5.72 mmol) in DMF (50 mL) was added KF (2.33 g, 40.04 mmol) followed by triethylamine (1.70 mL, 12.24 mmol) and di-tert-butyl dicarbonate (7.39 mmol), and the mixture was stirred at an ambient temperature.
T529 355-524 Sentence denotes After 4 h, TLC analysis indicated incomplete reaction and the reaction mixture was treated with a second portion of KF (2.7 g, 46.55 mmol) and BOC2O (800 mg, 3.67 mmol).
T530 525-607 Sentence denotes After 16 h, the mixture was diluted with diethyl ether (300 mL), washed with satd.
T531 608-940 Sentence denotes NaHCO3 (2 × 50 mL), 1 M hydrochloric acid (2 × 50 mL), NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and the solvents were evaporated in vacuo to yield the crude product, which was purified by Biotage flash chromatography eluting with dichloromethane/hexane to afford the title compound as a clear oil, 980 mg, 66%.
T532 941-1191 Sentence denotes 1H NMR (400 MHz, CDCl3) δ 4.96 (d, J = 6.8 Hz, 1H), 4.21–4.32 (m, 1H), 3.72 (s, 3H), 1.72–1.85 (m, 1H), 1.46–1.66 (m, 2H), 1.43 (s, 9H), 1.11–1.29 (m, 2H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (API-ES+) for C13H25NO4m/z 282.2 (M + Na)+.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1781 0-54 Chemical denotes Methyl N-(tert-Butoxycarbonyl)-5-methyl-l-norleucinate
1796 72-139 Chemical denotes methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucinate
1797 163-166 Chemical denotes DMF MESH:D004126
1798 221-234 Chemical denotes triethylamine MESH:C016162
1799 261-286 Chemical denotes di-tert-butyl dicarbonate MESH:C027600
1800 498-503 Chemical denotes BOC2O MESH:C027600
1801 566-579 Chemical denotes diethyl ether MESH:D004986
1802 602-606 Chemical denotes satd
1803 608-614 Chemical denotes NaHCO3 MESH:D017693
1804 632-649 Chemical denotes hydrochloric acid MESH:D006851
1805 663-669 Chemical denotes NaHCO3 MESH:D017693
1806 683-688 Chemical denotes brine MESH:C017082
1807 709-714 Chemical denotes MgSO4 MESH:D008278
1808 860-875 Chemical denotes dichloromethane MESH:D008752
1809 876-882 Chemical denotes hexane MESH:D006586