酰胺水解制备硫醚

solution of (R)-N-Methyl-3-phenylbutanamide (194 mg, 1.09 mmol) in methylene chloride was added triethylamine (0.15 ml, 1.09mmol), di-tert-butyl dicarbonate (0.5 ml, 2.18 mmol) and 4-(dimethylamino)pyridine (150 mg, 1.11 mmol). The solution was stirred for 8 h at room temperature. The volatiles were removed and the residue was purified by flash chromatogramphy (1/20 (v/v) EtOAc/hexane) to afford the desired (R)-N-Boc-N-Methyl-3-phenylbutanamide (210 mg, 70%).

A 0.2 M solution of (R)-N-Boc-N-Methyl-3-phenylbutanamide (175 mg, 0.63 mmol) in THF (4 ml), under N2 atmosphere, was cooled to 0°C. To this solution was added 1 N lithium hydroxide (2.0 ml, 2.0 mmol). The reaction mixture was allowed to stir for 6 h. After removal of THF in vacuo, the basic residue was acidified with 5% HCl and extracted with ether (3 ×15 ml). The combined ether layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by bulb-to-bulb distillation

(110~120°C/1.2 mmHg) to give the desired (R)-3-phenylbutyric acid (85 mg, 85%).

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