L-Hydroxyproline → HCID 15671477, compound

Participants

Reaction Steps

trans-4-Hydroxy-L-proline (13.1 g) and triethylamine (21 ml) were dissolved in 55 ml of water, and a solution of 33.44 g of S-p-methoxybenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in 55 ml of dimethylformamide was added thereto. The resulting mixture was stirred at room temperature for 12 hours, diluted with water and washed with ethyl acetate. The aqueous layer was acidified with 5N hydrochloric acid (pH 2) under ice-cooling and extracted with ethyl acetate. The extract was washed successively with dilute hydrochloric acid and brine, dried over anhydrous sodium sulfate and distilled to obtain trans-1-(p-methoxybenzyloxycarbonyl)-4-hydroxy-L-proline. IR maxneat cm-1 : 1670, 1435, 1350, 1240, 1168.

Provenance & Evidence