L-Phenylalanine → HCID 10943623, compound

Participants

Reaction Steps

Following the procedure of Block (J. Chem. Soc. (C), 329, (1971)), L-Phenylalanine (16.5 g, 100 mmol) was added to a solution of NaOEt (100 mmol) in absolute ethanol (1L). Salicylaldehyde (12.2 g, 100 mmol) was added and the yellow-green solution was concentrated in vacuo and dried under hi-vac for three h at 50° C. The residue was dissolved in 400 ml of EtOH-free CHCl3 and K2CO3 (138 g, 1 mol) was added. Mechanical stirring was started and a solution of triphosgene (11 g, 37mmol) in 100 ml CHCl3 was added dropwise such that the reaction temperature remained at or below 30° C. Stirring was continued for 2-3 h at which time the reaction was filtered and the salts were washed with several portions of solvent. The organic solution was washed with H2O, dried (MgSO4), and concentrated in vacuo. Recrystallization from ethyl acetate-hexane mixtures provided the title compound as a colorless solid (14.2 g, 48%). mp=158°-159° C.; [α]D =+150.25° (c=1, CH2Cl2); MS(DCI): 296(M+H)+.

Provenance & Evidence