L-Valine → HCID 36689750, compound

Participants

Reaction Conditions

Reaction Steps

L-Valine (5.86 g, 50 mmol) was dissolved in a mixture of water (200 mL) containing sodium carbonate (10.6 g, 100 mmol). The solution was cooled to 0° C., then a solution of isobutylchloroformate (6.76 g, 49.5 mmol) in dioxane (100 mL) was added dropwise over 50 min. The ice-bath was removed and the reaction stirred overnight. Dioxane was evaporated, the aqueous phase was extracted once with diethylether and the brought to pH 2 by addition of hydrochloric acid. Extraction with DCM (3×, 150 mL each), drying of the organic phase (sodium sulfate) and evaporation gave 21 (14.2 g) as a colorless solid. 1H-NMR (DMSO-d6) δ 12.48 (bs, 1 H), 7.24 (d, J=8.2 Hz, 1 H), 3.95 (dd, J=6.2, 8.3 Hz, 1 H), 3.73 (d, J=6.7 Hz, 1 H), 2.01 (m, 1 H), 1.83 (m, 1 H), 0.87 (bs, 12 H).

Provenance & Evidence