Sodium Hydroxide → [[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

Participants

Reaction Steps

To a suspension of benzyl [[(2S)-2-[[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]-acetate (10.8 g) in methanol (200 ml) was added 1N aqueous sodium hydroxide solution (22.6 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, and the residue was treated with aqueous citric acid solution (10%, 100 ml). The resulting white precipitate was collected by filtration, washed with tetrahydrofuran-hexane (1:1, 150 ml), and dried in vacuo to give the title compound (8.25 g) as a white solid.

Provenance & Evidence