Toluene → HCID 54339882, compound

Participants

Reaction Steps

1 g (5.06 mmol) of dibenzylamine and 1.73 ml (10.1 mmol) of Hunig base in 50 ml of methylene chloride were treated dropwise while cooling with ice with 2.6 ml of phosgene in toluene (20%. 5.06 mmol) and the solution obtained was stirred at 0° for 3 hours. Then, 1.1 g of L-phenylalanine methyl ester were added and the mixture was heated to 40° for 12 hours. Thereafter, the reaction mixture was poured into water, extracted with methylene chloride and the extracts were dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was chromatographed on silica gel using a 15:1 mixture of methylene chloride and ether as the eluting agent, to obtain 900 mg (45%) of N-(dibenzylcarbamoyl)-3-phenyl-L-alanine methyl ester as a white solid. MS: 402 (M)+.

Provenance & Evidence