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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of di-tert-butyl (4S)-4-allyl-N-(tert-butoxycarbonyl)-L-glutamate (345 mg, 0.86 mmol) in acetonitrile (5 ml) at room temperature was slowly added 1-(benzyloxy)-4-iodobenzene (ABCR GmbH & CO. KG) (321 mg, 1.04 mmol) in 3 ml acetonitrile, triethylamine (144 μl, 1.04 mmol) in 3 ml acetonitrile, and palladium(II) acetate (Aldrich) (39 mg, 0.17 mmol). The mixture was heated in a pressure tube at 80° C. for 2 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated in vacuo. The crude material was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Provenance & Evidence