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

Temperature

0 °C

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 S 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)+.

1. additionwas slowly added to the aqueous S mixture
2. customcoming to ambient temperature
3. extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-8f062eac550c4d5c9cafda1bc110c953

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006387B2