Hydrochloric Acid → (2S,4S)-1-(Tert-butoxycarbonyl)-4-(2,4-difluoro-phenoxy)-2-pyrrolidinecarboxylic acid

反応式

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH:9]1[C:22]([O:24]C)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH:9]1[C:22]([OH:24])=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

実験手順

To a stirred solution of methyl 1-(tert-butoxycarbonyl)-4-(2,4 difluorophenoxy)pyrrolidine-2-carboxylate (5.82 g, 16.3 mmol) in THF (130 ml) was added 0.25 N NaOH (130 ml, 32.6 mmol). The resulting mixture was stirred overnight. The mixture was poured into 1 N HCl (100 ml) and extracted with CHCl3 (2×200 ml). The extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)pyrrolidine-2-carboxylic acid (2.55 g, 46%) as a colorless foam. 1H-NMR (CDCl3) δ 1.42–1.47 (m, 9 H), 2.29–2.74 (series of m, 2 H), 3.66–3.71 (m, 2 H), 4.46–4.51 (m, 1 H), 4.83 (m, 1 H), 6.73–6.95 (m, 3 H).