Hydrochloric Acid → (2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldimethylsilyl)oxy]butanoic acid

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Reaction Steps

A solution of (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (614a) (1.07 g, 3.08 mmol) in THF (25 mL) was treated with 1.0 M aq. LiOH (6.16 mL, 6.16 mmol) and the mixture was stirred for 72 h. The mixture was diluted with saturated aq. brine (100 mL) containing 1.0 M aq. HCl (10 mL), and extracted into EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoic acid (614b) (1.03 g, 3.09 mmol, 100% yield) as a viscous colorless oil that crystallized upon standing. LC-MS m/z 356.1, [M+Na]+.

Provenance & Evidence