Triethylamine → HCID 178501369, compound

Participants

Reaction Conditions

Reaction Steps

D-Phenylalanine methyl ester hydrochloride (10 g, 0.046 mol) was suspended in a solution of triethylamine (33 mL) in dichloromethane (50 mL). The mixture was cooled to 0-5° C. and trans-4-isopropylcyclohexane carboxylic acid (7.9 g, 0.046 mol) was added. A solution of propane phosphonic acid anhydride (46.4 mL, 0.046 mol) in ethyl acetate was added dropwise over a period of 30 minutes, maintaining the temperature at 0-5°. The resulting mixture was stirred for 14 hours at ambient temperature. The reaction mixture was washed with 1.5 N HCl, 5% sodium bicarbonate solution and brine. The organic layer was concentrated to yield 12.5 g of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine methyl ester.

Provenance & Evidence