Water → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid

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Reaction Steps

Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate (2.0 g, 85.7 mmol) was dissolved in tetrahydrofuran (40 ml) and water (20 ml) and lithium hydroxide mono hydrate (1.8 g, 42.9 mmol) added. The mixture was stirred for 4 hours at room temperature, concentrated under reduced pressure to remove most of the tetrahydrofuran and then acidified by the addition of concentrated hydrochloric acid. The solution was extracted with ethyl acetate (three times). The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-O-methyl-D-serine (1.9 g, 100%) as a colourless oil; 1H NMR spectrum: (DMSO d6) 1.37 (s, 9H), 3.23 (s, 3H), 3.53 (m, 2H), 4.18 (m, 1H), 6.87 (d, 1H), 12.60 (brs, 1H).

Provenance & Evidence