Sodium Hydroxide → N-Boc-8-amino-2E-octenoic acid

Participants

Reaction Steps

A solution of 10.7 g (39.4 mmoles) of (8) in 30 mL methanol was chilled in an ice bath and 59 mL of 1N sodium hydroxide was added. The ice bath was removed and the mixture was stirred at room temperature for 20 h. After evaporation of most of the methanol, the solution was acidified to pH 3 with 1N potassium bisulfate. The mixture was extracted with ether, and washed with water and brine. After drying over sodium sulfate and removal of solvent in vacuo, the residue was crystallized from ether - hexane to provide 9.55 g of the title compound (9), mp 76°-78° C. Anal. Calcd. for C13H23NO4 : C, 60.68; H, 9.01; N, 5.44. Found: C, 60.50; H, 9:00; N, 5.40.

Provenance & Evidence