N-Carbobenzyloxy-L-glutamine synthesis
- Product Name:N-Carbobenzyloxy-L-glutamine
- CAS Number:2650-64-8
- Molecular formula:C13H16N2O5
- Molecular Weight:280.28
Yield:2650-64-8 98%
Reaction Conditions:
with sodium carbonate in 1,4-dioxane;water at 0 - 20;Inert atmosphere;
Steps:
(S)-5-amino-2-(benzyloxycarbonylamino)-5-oxopentanoic acid (11):
In 50 mL 1,4-dioxane and L- glutamine (10g, 0.068 mmol) solution at0oC added Na2CO3 (14.5g, 0.136 mmol) in 50 mL water and 22 mL (23.2g, 0.136 mmol) of benzylchloroformate. The reaction mixture was stirred overnight at roomtemperature and solvent was concentrated in vacuo,the mixture was washed three times with diethyl ether. The aqueous layer wasacidified with 2N HCl in water, the organic layer was extracted with EtOAc (3X100 mL), driedwith anhydrous sodium sulfate, and concentrated in vacuo gave the compound 11as off white solid(98% isolated yield);MS(ESI): m/z= 281 [M+H]+,303[M+Na]+.
References:
Yadav, Jhillu Singh;Dachavaram, Soma Shekar;Grée, René;Das, Saibal [Tetrahedron Letters,2015,vol. 56,# 26,art. no. 46176,p. 3999 - 4001] Location in patent:supporting information
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