L-Phenylalanine → N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Participants

Reaction Conditions

Reaction Steps

To an aqueous solution containing 13.2 g of potassium hydroxide dissolved in 330 ml of water was added 33.0 g (0.20 mole) of L-phenylalanine to form a solution. After being cooled to -5° C., the solution was fed little by little with 30.0 g (0.21 mole) of N-formyl-L-aspartic acid anhydride for one hour while maintaining its temperature at -5° C. to 5° C. A 10% aqueous sodium hydroxide solution was added thereto simultaneously to maintain the reaction liquid at a pH of 8-11. Thereafter, the reaction was carried out at the same temperature for one hour. The reaction mixture was analyzed by high speed liquid chromatography, with the result that the isomer formation ratio of N-formyl-α-L-aspartyl-L-phenylalanine to N-formyl-β- L-aspartyl-L-phenylalanine was 78:22 while the overall yield was 98% based on L-phenylalanine.

Provenance & Evidence