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 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 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-b7ea253d99094c65984805719c7245dd

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691938B2