Acetic Acid → tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate

Participants

Reaction Steps

1.25 g (9.2 mmol) of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride and 1.03 g (9.2 mmol) of potassium tert-butoxide were dissolved in 3 ml of absolute dimethylformamide and the mixture was stirred at room temperature for 30 min. 740 mg (1.53 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate (step c) in 1 ml of dimethylformamide were then added and the mixture was stirred at room temperature for 4 h. It was then adjusted to pH 4 using glacial acetic acid, the solvent was stripped off in vacuo, and the residue was chromatographed on silica gel (dichloromethane/methanol/glacial acetic acid/water (9/1/0.1/0.1)). Yield: 190 mg (38%).

Provenance & Evidence