Triethylamine → di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{(E)-3-[4-(3-hydroxypropyl)phenyl]prop-2-en-1-yl}-L-glutamate

Participants

Reaction Conditions

Reaction Steps

To a solution of di-tert-butyl (4S)-4-allyl-N-(tert-butoxycarbonyl)-L-glutamate (940 mg, 2.53 mmol) in 5 mL acetonitrile under an argon atmosphere was added 3-(4-iodophenyl)propan-1-ol (740 mg, 2.82 mmol), triethylamine (394 μl, 2.82 mmol), and palladium(II) acetate (106 mg, 0.47 mmol). The mixture was stirred in a pressure tube at 80° C. for 2 h. After cooling to room temperature, the solvent was removed under reduced pressure and the crude material was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Provenance & Evidence