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LitCovid-PD-FMA-UBERON

{"project":"LitCovid-PD-FMA-UBERON","denotations":[{"id":"T85","span":{"begin":56,"end":63},"obj":"Body_part"},{"id":"T86","span":{"begin":229,"end":238},"obj":"Body_part"}],"attributes":[{"id":"A85","pred":"fma_id","subj":"T85","obj":"http://purl.org/sig/ont/fma/fma82749"},{"id":"A86","pred":"fma_id","subj":"T86","obj":"http://purl.org/sig/ont/fma/fma82749"}],"text":"N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)\nA 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. 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. 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. 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. 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%. 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-PD-CLO

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T375","span":{"begin":68,"end":71},"obj":"http://purl.obolibrary.org/obo/CLO_0001577"},{"id":"T376","span":{"begin":458,"end":459},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T377","span":{"begin":504,"end":505},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T378","span":{"begin":889,"end":890},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T379","span":{"begin":911,"end":919},"obj":"http://purl.obolibrary.org/obo/OBI_0100026"},{"id":"T380","span":{"begin":911,"end":919},"obj":"http://purl.obolibrary.org/obo/UBERON_0000468"},{"id":"T381","span":{"begin":1010,"end":1018},"obj":"http://purl.obolibrary.org/obo/OBI_0100026"},{"id":"T382","span":{"begin":1010,"end":1018},"obj":"http://purl.obolibrary.org/obo/UBERON_0000468"},{"id":"T383","span":{"begin":1119,"end":1120},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T384","span":{"begin":1291,"end":1293},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T385","span":{"begin":1327,"end":1332},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)\nA 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. 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. 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. 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. 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%. 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-PD-CHEBI

LitCovid-sentences

{"project":"LitCovid-sentences","denotations":[{"id":"T255","span":{"begin":0,"end":67},"obj":"Sentence"},{"id":"T256","span":{"begin":68,"end":356},"obj":"Sentence"},{"id":"T257","span":{"begin":357,"end":559},"obj":"Sentence"},{"id":"T258","span":{"begin":560,"end":747},"obj":"Sentence"},{"id":"T259","span":{"begin":748,"end":933},"obj":"Sentence"},{"id":"T260","span":{"begin":934,"end":1137},"obj":"Sentence"},{"id":"T261","span":{"begin":1138,"end":1335},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)\nA 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. 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. 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. 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. 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%. 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

{"project":"LitCovid-PubTator","denotations":[{"id":"923","span":{"begin":0,"end":63},"obj":"Chemical"},{"id":"937","span":{"begin":166,"end":238},"obj":"Chemical"},{"id":"938","span":{"begin":284,"end":292},"obj":"Chemical"},{"id":"939","span":{"begin":342,"end":345},"obj":"Chemical"},{"id":"940","span":{"begin":346,"end":350},"obj":"Chemical"},{"id":"941","span":{"begin":357,"end":361},"obj":"Chemical"},{"id":"942","span":{"begin":379,"end":384},"obj":"Chemical"},{"id":"943","span":{"begin":642,"end":659},"obj":"Chemical"},{"id":"944","span":{"begin":729,"end":737},"obj":"Chemical"},{"id":"945","span":{"begin":777,"end":790},"obj":"Chemical"},{"id":"946","span":{"begin":830,"end":847},"obj":"Chemical"},{"id":"947","span":{"begin":965,"end":978},"obj":"Chemical"},{"id":"948","span":{"begin":1036,"end":1041},"obj":"Chemical"},{"id":"949","span":{"begin":1054,"end":1059},"obj":"Chemical"}],"attributes":[{"id":"A938","pred":"tao:has_database_id","subj":"938","obj":"MESH:D000432"},{"id":"A939","pred":"tao:has_database_id","subj":"939","obj":"MESH:D007053"},{"id":"A940","pred":"tao:has_database_id","subj":"940","obj":"MESH:D012965"},{"id":"A942","pred":"tao:has_database_id","subj":"942","obj":"MESH:D014867"},{"id":"A943","pred":"tao:has_database_id","subj":"943","obj":"MESH:D006851"},{"id":"A944","pred":"tao:has_database_id","subj":"944","obj":"MESH:D000432"},{"id":"A945","pred":"tao:has_database_id","subj":"945","obj":"MESH:C007650"},{"id":"A946","pred":"tao:has_database_id","subj":"946","obj":"MESH:D006851"},{"id":"A947","pred":"tao:has_database_id","subj":"947","obj":"MESH:C007650"},{"id":"A948","pred":"tao:has_database_id","subj":"948","obj":"MESH:C017082"},{"id":"A949","pred":"tao:has_database_id","subj":"949","obj":"MESH:D008278"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"N-(tert-Butoxycarbonyl)-3-[(3S)-2-oxopyrrolidin-3-yl]-l-alanine (6)\nA 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. 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. 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. 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. 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%. 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)−."}