Abstract
An efficient two-step synthesis of 4(5)-benzyl- l -histidine from l -histidine was developed. A Pictet–Spengler reaction between l -histidine and benzaldehyde in the presence of excess strong base yielded 4- l -phenylspinacine within one hour. Catalytic transfer hydrogenolysis in methanol at reflux using ammonium formate rapidly converted 4- l -phenylspinacine to 4(5)-benzyl- l -histidine within five minutes. No racemization of the final product 4(5)-benzyl- l -histidine was observed using the Marfey reagent. To show the utility of this method, a series of fluorinated benzylhistidines were prepared.
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