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.
Original language | English (US) |
---|---|
Article number | SS-2013-M0680-OP |
Pages (from-to) | 515-521 |
Number of pages | 7 |
Journal | Synthesis (Germany) |
Volume | 46 |
Issue number | 4 |
DOIs | |
State | Published - Feb 2014 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry