Sodium Carbonate → (S)-2-Phthalimido-6-hydroxyhexanoic acid

Participants

Reaction Steps

A solution of (+)-L-ε-hydroxynorleucine [prepared according to the procedure of Bodanszky et al., J. Med Chem., 1978, 21, 1030-1035](1.030 g., 7.0 mmol.) and sodium carbonate (745 mg., 7.0 mmol.) in water (12 mL) was treated with N-carbethoxyphthalimide (1.495 g., 7.0 mmol.) and the mixture was stirred at room temperature for 2 hours. The solution was filtered, cooled to 0° C., and acidified with 6N hydrochloric acid to afford a white precipitate. The solid was collected by filtration and dried in vacuo at 80° C. for 1 hour to give 1.297 g. of the title compound; m.p. 162°-163° C.; [α]D =-35.7° (c=1.3, methanol).

Provenance & Evidence