Water → HCID 86592524, compound

Participants

Reaction Steps

To a solution of tert-butyl (4S)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate (5.29 g, 1.2 mmol) in methanol (106 ml) was added p-toluenesulfonic acid monohydrate (0.22 g, 1.2 mmol) and the mixture was stirred for 30 minutes. To the mixture was further added p-toluenesulfonic acid monohydrate (0.22 g, 1.2 mmol) and the mixture was stirred for 1 hour. The reaction mixture was poured into water and extracted three times with ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography to give tert-butyl (4S)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino]-5-hydroxypentanoate (3.7 g, 93%).

Provenance & Evidence