Water → HCID 57972811, compound

Participants

Reaction Steps

2.91 g (12.0 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6 was dissolved in methanol (15 mL) and further mixed with water (10 mL) and potassium hydroxide (1.34 g, 23.9 mmol). The resulting solution was stirred at room temperature for 14 hours. On completion of the reaction, methanol was removed by distillation and toluene (10 mL) and water (5 mL) were added to separate the solution. The separated organic layer was further mixed with water (15.2 mL) and a 30 wt % aqueous solution of potassiumhydroxide (1.02 g) to separate the solution again. The separated aqueous layers were collected together and adjusted to be pH=1.5 by concentrated hydrochloric acid and extraction with toluene (20 mL) was repeated three times. The residue obtained by concentrating the organic layer was crystallized from toluene (9 mL)/hexane (35 mL) to obtain (R)-3-[4-(trifluoromethyl)phenylamino]-pentanoic acid as awhite crystal (2.38 g, isolated yield: 76%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 0.90 (3H, t), 1.5-1.8 (2H, m), 2.4-2.5 (2H, m), 3.7-3.9 (1H, m), 6.65 (2H, d), 7.39 (2H, d)

Provenance & Evidence