N-acetyl-N-methyl-L-alanine methyl ester → N-Acetyl-N-methyl-L-alanine

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Reaction Steps

The ester obtained above is dissolved in a mixture of 100 ml methanol and 170 ml 1 N-aqueous sodium hydroxide. The solution is allowed to stand at a room temperature for 2 hours, and the methanol is removed under reduced pressure. The alkaline aqueous solution is extracted with chloroform. The water layer is brought to pH 1 with concentrated hydrochloric acid under ice-cooling and extracted with ethyl acetate (140 ml×5). The extract is dried over anhydrous sodium sulfate and concentrated under reduced pressure to recover a white solid. Recrystallization from ethyl acetate-hexane yields 8.1 g of N-acetyl-N-methyl-L-alanine as colorless needles.

Provenance & Evidence