Hydrochloric Acid → tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate

Participants

Reaction Steps

To a solution of tert-butyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate (14.26 g, 46.1 mmol) in dichloromethane (190 ml) were added under ice cooling 4-dimethylaminopyridine (0.28 g, 2.3 mmol), diisopropylethylamine (24 ml, 138 mmol) and chloromethyl methyl ether (105 ml, 138 mmol). The mixture was raised to room temperature. Twelve hours later, to the mixture were added ice water and 1N hydrochloric acid under cooling in an ice bath to adjust pH to about 3. To the mixture was added a saturated aqueous sodium chloride solution and the solution was separated with a separating funnel. The organic layer was washed once with water and twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate (16.4 g, 100%).

Provenance & Evidence