Benzyl Alcohol → 5-(Phenylmethyl) hydrogen D-glutamate

Participants

Reaction Steps

To a solution of 29.1 g (1.0 eq) H-D-Glu-OH in 205.6 mL (10.0 eq) benzyl alcohol which was stirred at r.t, 47.7 mL (2.0 eq) boron trifluoride etherate solution was added slowly, and 10 min later, all of the substrate was dissolved. The reaction was completed in 15 h, 616.8 mL (3 times of the volume of benzyl alcohol) THF was added, stirred and 55.1 mL (2.0 eq) triethylamine was added slowly. A large number of white viscous precipitate precipitated. The THF was removed under reduced pressure; the residue was cooled, after adding the proper amount of the AcOEt, the viscous precipitate turned to powder. 36.6 g target compound was obtained with yield of 78% after filtration and drying. m.p.=174˜176° C.

Provenance & Evidence