Dichloromethane → 2-(S)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester

반응식

F[C:2](F)(F)[C:3]([OH:5])=[O:4].[CH2:8]([O:10][C:11](=[O:40])[C@H:12]([CH:19](COC(=O)C)[C:20]1[CH:25]=[CH:24][C:23]([NH:26]C(OC(C)(C)C)=O)=[C:22]([CH3:34])[CH:21]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:9].Cl[CH2:42]Cl>>[CH2:8]([O:10][C:11](=[O:40])[C@@H:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:34])[C:21]=1[CH2:42][O:5][C:3](=[O:4])[CH3:2])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:9]

참가 물질

반응물 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 673188002-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester

생성물 1

HCID 597319272-(S)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester수율 99%

실험 절차

Trifluoroacetic acid (10 mL) was added to a solution of 2-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester (4.6 g, 9.9 mmol) in dichloromethane (40 mL). Reaction mixture was stirred at room temperature for 1.5 hours. Mixture was concentrated in vacuo. Residue was dissolved in dichloromethane (75 mL) and washed successively with saturated aqueous sodium bicarbonate (2×50 mL) and brine (30 mL). Organic was dried (magnesium sulfate), filtered and concentrated in vacuo to yield the desired product in 99% yield as an amber oil. 1H NMR (300 MHz, CDCl3): δ=6.85 (d, J=8.1, 1H), 6.67 (d, J=8.4, 1H), 5.18 (m, 2H), 4.09 (m, 4H), 3.09 (dd, J1=6.2, J2=13.9, 1H), 2.96 (m, 1H), 2.66 (m, 2H), 2.37 (dd, J1=4.6, J2=16.7, 1H), 2.15 (s, 3H), 2.06 (s, 3H), 1.20 (m, 6H). MS m/e (M−C2H4O2+H)+=306.2.