Hydrochloric Acid → (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochloride

반응식

[CH:1]1([CH2:6][C@@H:7]([C:16](=[O:31])[N:17]2[C@H:21]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[O:23])[CH2:20][CH:19]=[N:18]2)[CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:32].O1CCOCC1>>[ClH:32].[CH:1]1([CH2:6][C@@H:7]([C:16](=[O:31])[N:17]2[C@H:21]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[O:23])[CH2:20][CH:19]=[N:18]2)[CH2:8][C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 867064101,1-Dimethylethyl (3R)-3-(cyclopentyl methyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoate

생성물 1

HCID 131732111(3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochloride수율 100%

실험 절차

To a 500 ml round bottom flask was added 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoate (29.1 g, 58.4 mmol) and 4 M HCl in 1,4-dioxane (240 mL, 960 mmol). The mixture was stirred at room temperature and monitored by LCMS. After 90 min, no starting material remained. The mixture was concentrated to dryness and co-evaporated with dioxane (2×15 mL) to afford the crude (3R)-3-(cyclopentylmethyl)-4-oxo-4-{(5S)-5-[(2-pyridinylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid, hydrochloride (34.0 g, 58.5 mmol, 100% yield) as a light brown foamy solid that was used directly for the next step. LCMS: [M+H]+: 373.2.