L-Valine → (2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

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Reaction Steps

5.67 g (60 mmol) of chloroformic acid methyl ester are added to 7.0 g (60 mmol) of L-valine in 100 ml of 2N NaOH and 30 ml of dioxane (→exothermic reaction) and the mixture is then stirred for 18 h at RT. The reaction mixture is extracted with methylene chloride and the aqueous phase is acidified with 27 ml of 4N HCl and extracted again with methylene chloride. Drying and concentration by evaporation of the latter methylene chloride phase yields the title compound: tRet (I)=7.2 min; 1H-NMR (200 MHz, CD3OD): 0.96 (t, J=7 Hz, 6H), 2.16 (m, 1H), 3.67 (s, 3H), 4.06 (m, 1H), 7.07 (d, J=8 Hz, HNpartially exchanged).

Provenance & Evidence