Hydrochloric Acid → (2S,3S)-2-Chloro-3-methylvaleric Acid

Participants

Reaction Steps

To a cooled (0° C.) solution of L-Isoleucine (40 g) dissolved in HCl (5N, 750 ml) was added dropwise a solution of sodium nitrite (35 g in 100 ml water). The reaction was stirred overnight at room temperature (˜23° C.), Na2CO3 (31 g) slowly added and the reaction mixture extracted with EtOAc (3×150 ml). The combined organic extracts washed with water, half saturated brine, dried over MgSO4, filtered and concentrated. The product a yellowish oil was distilled under reduced pressure (5 torr, bp=111° C.) to afford a colorless oil (32 g) obtained in 70% yield. (see FIG. 6).

Provenance & Evidence