Benzaldehyde → HCID 53992031, compound

Participants

Reaction Steps

A solution of (3S) 2-oxo-3-amino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester hydrochloride (560 mg, 1.34 mmol), benzaldehyde (146 mg, 1.34 mmol) and sodium acetate (220 mg, 2.68 mmol) in methanol (20 ml) was treated with 4A sieves (2 g) and NaCNBH3 (168 mg, 2.68 mmol). The reaction was stirred for 2.5 h, acidified with 10 aq. HCl to pH 2 and washed with Et2O (2×75 ml). The organic layers were concentrated in vacuo to give an oil. Chromatography (flash, SiO2, 0 to 35% EtOAc/CH2Cl2) gave 250 mg (40%) of 602v as a clear oil.

Provenance & Evidence