ETHYL 2-((BENZYLOXYCARBONYL)(ETHYL)AMINO)ACETATE synthesis

Yield:-

Reaction Conditions:

in N-methyl-acetamide;dichloromethane;

Steps:

19.i (A)

(i) In a manner analogous to that described in J. Org. Chem. 35, page 1914 (1970), 10.45 g (50 mmol) of N-benzyloxycarbonyl-glycine was stirred in 100 ml of dry dimethylformamide at room temperature and treated with 62.4 g (400 mmol) of ethyl iodide and ca 46 g (180 mmol) of silver oxide. The mixture was stirred overnight and filtered, the filtrate was diluted with 400 ml of methylene chloride and refrigerated overnight. The precipitated silver iodide was filtered off and the filtrate was washed twice with 100 ml portions of aqueous potassium cyanide solution and then three times with 150 ml portions of water. The organic layer was dried over sodium sulphate, filtered and evaporated, first at the water pump and then at the oil pump, to give 14.25 g of crude ethyl N-benzyloxycarbonyl-N-ethyl glycinate in the form of a yellow oil.

References:

US4250085,1981,A