Triethylamine → methyl N-(p-nitrobenzyloxycarbonyl)-alpha-methoxyglycinate

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Reaction Steps

Triethylamine (5.06 g, 0.05 mole) and p-nitrobenzyl chloroformate (10.78 g, 0.05 mole) are added to an ice-cold solution of methyl α-methoxyglycinate (6.10 g, 0.05 mole) in dry CH2Cl2 (100 ml). The resulting mixture is stirred in the cold and under N2 for 2 hours, and then washed with 3 portions of water. The CH2Cl2 phase is dried over MgSO4, filtered, and evaporated in vacuo. Recrystallization of the residue affords pure methyl N-(p-nitrobenzyloxycarbonyl)-α-methoxyglycinate.

Provenance & Evidence