Cbz-N-methyl-L-valine

Chemical Properties

White powder

Uses

(S)-N-(Benzyloxycarbonyl)-N-methylvaline has been used as a reactant in the synthesis of a biologically active cyclodepsipeptide destruxin E which is a potent negative regulator of osteoclast morphology.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Under argon atmosphere, 60% sodium hydroxide (5 g, 0.125 mol) was added in one portion to a stirred mixture of Cbz-L-valine (9.5 g, 0.038) in anhydrous THF (150 mL) at 0C and stirred simultaneously for 30 minutes. mol) in anhydrous THF (150 mL) and stir for 30 minutes. Iodomethane (20 mL, 0.32 mol) was added and the resulting mixture was stirred overnight at room temperature. Ice water (200mL) was poured into the mixture at 0C and the resulting mixture was extracted with ether (2x200mL). The aqueous layer was acidified to pH using dilute HCl solution 1.5 and extracted with ethyl acetate (3x200mL). The combined organic extracts were washed with saturated sodium thiosulfate solution (100 mL), dried (Na2SO4) and evaporated in vacuo to give N and evaporated in vacuum to give N-Cbz-N-methyl-L-valine (5 g, 55%) as a colorless viscous oil which can be used in the next step without purification.