Hydrochloric Acid → HCID 28285778, compound

Participants

Reaction Steps

A solution of 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXIII) (30 g, 109 mol) in 1 M NaOH (50 mL) and water (1 L) was adjusted to pH 7.6-7.8 before adding CoCl2 (300 mg, 2.3 mmol) and Acylase I (3 g) (from Aspergilus melleus). The reaction was stirred at room temperature under argon for 2 days at which time Marfey's test was performed and additional enzyme (1 g) was added and the reaction was stirred for an additional day. The mixture was acidified with 2 M HCl to pH 1 and extracted with EtOAc (3×) (the aqueous phase containing the L-enantiomer (LXIV) was saved). The combined organic extracts were washed with 2 M HCl (3×), brine (3×) and dried over MgSO4. The solvent was removed under reduced pressure and the residue was recrystallized from EtOAc/hexane, affording (R)-2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXV) (10.2 g, 37 mmol, 68% yield).

Provenance & Evidence