[CH3:1][O:2][C:3]([NH:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[H-].[Na+].[CH2:13](Cl)[C:14]#[CH:15].[Cl-].[Na+]>CN(C)C=O>[CH2:15]([N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:14]#[CH:13]3.0 g of methyl N-methoxycarbonylglycinate were dissolved in 30 ml of N,N-dimethylformamide. Ice-cooling the mixture, 820 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere and stirred for 20 minutes. Then 2.3 g of propargyl chloride were dropped thereto over 10 minutes and further stirred for 40 minutes. The reaction mixture was poured into ice-water and then sodium chloride was added thereto to saturate the same. Thereafter the aqueous layer was washed with hexane and it was subjected to two 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 1.95 g of methyl N-propargyl-N-methoxycarbonylglycinate.
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