Water → (2S)-2-{[(Benzyloxy)carbonyl]amino}pent-4-enoic acid

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Reaction Steps

To a suspension of L-2-amino-4-pentenoic acid (2.0 g) in Dioxane (80 mL) at RT was added triethylamine (4.3 g), water (2.0 mL), and N-(benzyloxycarbonyloxy)succinimide (9.1 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NaHCO3 and extracted with ether (3×). The basic aqueous layer was acidified to pH 2 with 2N HCl and extracted with EtOAc (3×). The combined EtOAc layer was washed with brine, dried (Na2SO4), filtered and evaporated, then concentrated from Toluene (2×) to give a viscous oil (4.51 g, quantitative). 1H NMR (300 MHz, DMSO-d6) δ 2.31-2.50 (m, 2H), 4.00-4.06 (m, 1H), 5.03 (s, 2H), 5.05-5.12 (m, 2H), 5.71-5.84 (m, 1H), 7.35 (m, 5H), 7.53 (d, 1H), 12.57 (bs, 1H). MS APCI, m/z=250 (M+1). LC/MS 2.30 min., Method A.

Provenance & Evidence