Ethanol → HCID 86742759, compound

Participants

Reaction Steps

A mixture of 8.9 g (0.023 mol) of (±)-(S*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid methyl ester, 50 ml ethanol and 140 ml 1N sodium hydroxide was heated at reflux for 30 minutes. The reaction mixture was cooled to room temperature, diluted with water (50 ml) and extracted with ether (2×75 ml). The aqueous solution was chilled, then neutralized with acetic acid and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with water (75 ml) and dried (MgSO4). Removal of the solvent gave 8.2 g (96%) of (±)-(S*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, mp 167°-168°. The analyzed sample was recrystallized from ethyl acetate, mp 167°-168°.

Provenance & Evidence