782441-07-0Relevant articles and documents
An efficient synthesis of 4(5)-benzyl- L -histidines employing catalytic transfer hydrogenolysis at elevated temperatures
Smith, D. David,Gallagher, Audrey T.,Crowley, Vincent M.,Gergens, Wayne M.,Abel, Peter W.,Hulce, Martin
, p. 515 - 521 (2014/03/21)
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.
