Benzoyl chloride → HCID 14696315, compound

Participants

Reaction Steps

13.3 g of (2R)-N-(α,α-dimethylbenzyl)-2-(t-butoxycarbonylamino)-3-(p-methoxybenzylthio)propionamide (prepared as described in Preparation 6) were dissolved in 50 ml of toluene. To this solution were added 4.70 ml of triethylamine, and then 2.23 g of benzoyl chloride was added slowly to the mixture, whilst ice-cooling. The reaction solution was stirred for 70 minutes, and then ethyl acetate was added to it, after which it was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by column chromatography through 210 g of silica gel. From the fraction eluted with hexane containing 30-40% v/v ethyl acetate, were obtained 4.31 g of an oily substance. This substance was dissolved in a mixture of ethyl acetate and hexane, and, after removal of crystals which had separated out (about 250 mg, melting at 189° C.), concentration of the mother liquor gave 3.61 g of the title compound as a glassy substance, [α]25 =-25.3° (C=1, CHCl3).

Provenance & Evidence