Hydrochloric Acid → (2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-2-amino-3-methylbutanoic acid (10.0 g, 85.0 mmol), NaOH (3.41 g, 85.0 mmol) and NaHCO3 (4.7 g, 44.4 mmol) in H2O (85 mL) was cooled to 0° C. A mixture of methyl chloroformate (7.3 mL, 94.0 mmol) dissolved in Et2O (40 mL) was slowly added to the aqueous mixture and stirred for 20 hours coming to ambient temperature. Mixture was adjusted to pH 2.0 with HCl (conc). The mixture was extracted with CH2Cl2 (3×100 mL) and then dried (MgSO4), filtered and concentrated to afford 7.5 g (50%) of the title compound. MS (ESI) m/z 176 (M+H)+.

Provenance & Evidence