BOC-GLU-OME

White to off-white crystalline powder

Boc-L-glutamyl(OBn)(OMe)4 (4.95 g, 14.09 mmol) was dissolved in MeOH (20 mL) in a 50 mL roundbottom flask and 10percent palladium on carbon was added under nitrogen. The vesselwas purged three times with nitrogen and with hydrogen. Then, the mixture was stirredfor 6 hours under hydrogen at atmospheric pressure. The catalyst was removed by filtration and the filtrate wasevaporated to obtain compound 5 as acolorlessgummy liquid. (3.5 g, 96percent).[α]Step 2To a solution of 5-benzyl 1-methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}pentanedioate XIII (4.2 g, 12.23 mmol) in EtOH/water (40 mL/6 mL) under argon was added 10percent Pd/C catalyst (catalytic amount). The mixture was stirred under an atmosphere of hydrogen for 6 h at r.t. The mixture was then filtered through Celite and evaporated to dryness to afford the free acid (3.0 g, 11.48 mmol, 32percent yield). ESIMS found for CStep 2[00182] To a solution of 5-benzyl 1-methyl (2S)-2-{[(tert-butoxy)carbonyl] amino} pentanedioate XIII (4.2 g , 12.23 mmol) in EtOH/water (40 mL/6 mL) under argon was added 10percent Pd/C catalyst (catalytic amount). The mixture was stirred under an atmosphere of hydrogen for 6 h at room temperature. The mixture was then filtered through Celite and evaporated to dryness to afford the free acid (3.0 g, 11.48 mmol, 32percent yield). ESIMS found for CL-glutamic acid (38 g, 0.26 mol) was dissolved in anhydrous methanol (450 mL).Me3SiCl was added dropwise on ice bath (120 mL, 0.94mmol), Stir at room temperature overnight.Add Et3N (230 mL, 1.66 mol) and (Boc)2O (63.5 g, 0.3 mol) stirring at room temperature For an 3 hours, the concentrated column was evaporated to dryness to give compound L-1 (67.6 g, 95percent).

N-Boc-L-glutamic Acid α-Methyl Ester is a glutamate derivative that undergoes vitamin K-dependent carboxylation in liver microsomes.