29022-11-5

white to light yellow crystal powde

N-Fmoc-glycine is an N-Fmoc-protected form of Glycine (G615990). Glycine is a nonessential amino acid that acts as an inhibitory neyrotransmitter in the vertebrate central nervous system. Glycine also posesses cytoprotective against oxidant damage in the kidney.

Glycine (Gly) (0.5 g, 6.66 mmol) was dissolved in 10% NaCO₃ (14 ml) under stirring in a 50-ml flask. To the resulting solution, which had been put into an ice bath, 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) (1.72 g, 6.66 mmol) in dioxane (12 ml) was gradually added. The reaction mixture was stirred at room temperature for 4 hours. Then added water (150 ml) to the mixture. The aqueous phase layer was separated from the reaction mixture and stripped with ether three times (75 ml×3). The stripped aqueous layer was acidified with 2N HCl aqueous solution to a pH=2, followed by extraction with ethyl acetate three times (75 ml×3). The organic phase layer was recovered and concentrated to obtain crude product of 1.70 g. The crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid denoted as Fmoc-Gly-OH was obtained after filtration at a reduced pressure.