PMC:7571312 / 40032-41712
Annnotations
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 |