Methyl L-phenylalaninate hydrochloride → L-Phenylalanine

Participants

Reaction Steps

γ-Nitro-α-ethylbutyric acid 3 (97 mg, 0.6 mmol) was dissolved in dry dichloromethane (20 ml). Then L-Phe-OMe.HCl (142 mg, 0.66 mmol), EDCI.HCl (138 mg, 0.72 mmol), DIEA (128 uL, 0.72 mmol) and catalytic amount of DMAP were successively added. The mixture was stirred 24 h at room temperature, then was acidified with aqueous NaHSO4, extracted with EtOAc (3×). The organic layers were washed with saturated NaHCO3 and brine. The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography eluted with EtOAc/hexane to give L-phenylalanine derivative 7 as a while solid.

Provenance & Evidence