Dimethylformamide → N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1 g (3.31 mmol) of 3-(4-methoxyphenylsulfanyl)-4-phenylbutyric acid in 30 mL of CH2Cl2 at 25° C. under argon is added 0.2 mL of DMF followed by 4.1 mL (8.27 mmol) of 2 M solution of oxalyl chloride in CH2Cl2. After stirring at 25° C. for 1.5 hours, 2.1 mL (16.53 mmol) of O-trimethylsilylhydroxylamine is added and this is then stirred at 25° C. for 18 hours. The reaction is partitioned between CH2Cl2 and 1 N HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash silica gel chromatography affords 0.86 g (82%) of N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide as a yellow crystalline solid.

Provenance & Evidence