Hydrochloric Acid → (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate

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Reaction Steps

A solution of N-(tert-butoxycarbonyl)-L-threonine methyl ester (Aldrich) (717 mg, 3.07 mmol) in DCM (10 mL) was cooled in an ice-water bath and treated with 2,6-dimethylpyridine (Aldrich) (1.07 mL, 9.22 mmol) followed by tert-butyldimethylsilyl trifluoromethanesulfonate (Fluka) (0.85 mL, 3.69 mmol). The solution was stirred for 16 h, poured into 1 M aq. HCl (100 mL), and extracted with DCM (2×50 mL). The organic extracts were washed with saturated aq. NaHCO3 (100 mL), dried (MgSO4), filtered, and concentrated to give (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (614a) (1.07 g, 3.08 mmol, 100% yield) as a colorless oil.

Provenance & Evidence