[CH3:1][O:2][C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[H-].[Na+].[CH2:14](Br)[C:15]#[CH:16].O>CN(C)C=O>[CH2:16]([N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:15]#[CH:14]100 g of ethyl N-methoxycarbonylglycinate were dissolved in 600 ml of N,N-dimethylformamide. Then ice-cooling the mixture, 25 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere. After the reaction mixture was stirred for 2 hours, 81.3 g of propargyl bromide were dropped thereto over 2 hours. After the mixture was further stirred for an hour, the reaction product was poured into water and the aqueous layer was washed with hexane. Then it was subjected to three times of extraction with 100 ml of ether. The ether layers were combined together and dried over anhydrous magnesium sulfate and the solvent was evaporated off to obtain 79.8 g of ethyl N-propargyl-N-methoxycarbonylglycinate.
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