(S)-2-amino-1-(3-chlorophenyl)ethanol → HCID 69425530, compound

Participants

Reaction Conditions

Reaction Steps

(S)-(2E and 2Z)-2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-but-2-enedioic acid diethyl ester: To a stirred solution of (2-E and 2Z)-2-methanesulfonyloxy-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-but-2-enedioic acid diethyl ester (0.012 g, 0.021 mmol) in acetonitrile (1 mL) was added (S)-2-amino-1-[3-chlorophenyl]ethanol (0.005 g, 0.031 mmol) and the mixture was stirred at 60° C. for 1 hour. The solvent was evaporated and the residue was purified by silica gel chromatography (50 to 75% ethyl acetate in hexane) to give the title material (0.010 g, 74%). HPLC: 97% (220 nm), LCMS (+ESI, M+H+) m/z 657; 1H NMR (400 MHz, acetone-d6) δ (ppm): 1.17-1.33 (15H, m), 2.51 (3H, br s), 3.14 (4H, m), 3.77 (6H, m), 4.24-4.34 (4H, m), 5.62 (1H, m), 6.80-7.52 (6H, m).

Provenance & Evidence