Hydrochloric Acid → HCID 86660243, compound

Participants

Reaction Steps

To a solution of ethyl (5S)-5-{[(S)-tert-butylsulfinyl]amino}-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate (113 mg, 0.289 mmol, prepared by direct analogy to the methyl ester version according to U.S. Patent Application Publication No. US 2007/0265225) in MeOH (6 mL), cooled to 0° C., was added excess anhydrous, gaseous HCl over 1 minute via a rapid stream of bubbles. After 30 min, a stream of nitrogen was passed over the solution to remove some HCl. The reaction was then concentrated in vacuo. The residue was diluted with DCM (20 mL) and washed with saturated sodium bicarbonate (10 mL). The bicarbonate layer was subsequently extracted twice with DCM (10 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo, to yield a residue, containing about 30% methyl ester, which was used without further purification. MS: m/z=286 (M+1).

Provenance & Evidence