Water → Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate

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Reaction Steps

To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-hydroxypentanoate (5.7 g) and 2,6-lutidine (2.27 mL) in THF (80 mL) was added under ice-cooling tert-butyldimethylsilyl trifluoromethanesulfonate (3.44 mL) and, after warming to room temperature, the mixture was stirred for 17 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→32/1) to give the title compound as a colorless oil (yield: 5.42 g, 70%).

Provenance & Evidence