Acetic Anhydride → N-Acetyl-L-proline

Participants

Reaction Steps

To a suspension of L-Pro (247 mg, 2.15 mmol) in pyridine (1 ml) was added acetic anhydride (I ml), and the mixture was stirred at room temperature for 5 min. The solvent was removed in vacuo and the resulting oil was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was dried over sodium sulfate, and concentrated, and the resulting solid was recrystallized from ethyl acetate to give N-acetyl-L-proline (167 mg, 44%), a white powder: m.p. 108° C. [lit 115° C. (from CHCl3)99 ]; [α]D25 -171° (c, 0.91, CHCl3) [(lit107 -118° (c, 1, H2O)] Anal. Calcd. for C7H11NO3 : C, 53.49; H, 7.05, N, 8.91. Found: C, 53.57; H, 7.09; N, 8.76.

Provenance & Evidence