Benzyloxycarbonylglycine → HCID 70043751, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3.7 g of (S)-2-oxopiperazine-1,3-diacetic acid di-t-butyl ester hydrochloride, 3.3 g of N-benzyloxycarbonyl glycine and 10 ml of dimethylformamide were added dropwise, while stirring at 0° C., 3.1 g of diethyl cyanophosphonate then 3.2 g of triethylamine in the course of 10 minutes. The mixture was stirred for one hour at the same temperature then for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product was dissolved in 30 ml of methanol, to which were added 1 g of 10% palladium-carbon and 1.8 ml of 4N HCl-dioxane solution. The mixture was stirred for one hour at room temperature under hydrogen. The catalyst was removed, and the reaction mixture was concentrated under reduced pressure to afford 2.6 g of the title compound as a colorless oily product. This product was processed with ether to give colorless powder.

Provenance & Evidence