Methanol → Methyl N-acetyl-DL-phenylalaninate

Beteiligte Stoffe

Reaktionsschritte

Into a 100 milliliter round bottom flask were placed 10.36 grams (50 millimoles) of N-acetyl-D,L-phenylalanine, 48 grams (1.5 moles) of methanol and 2 grams of sulfuric acid (0.02 moles). The mixture was refluxed for 3 hours. The solvent was then removed under vacuum and the resulting oily residue was taken up in 100 milliliters of ether, washed with 50 milliliters of 5% sodium bicarbonate, 50 milliliters of saturated sodium chloride solution, dried over magnesium sulfate, filtered and the solvent removed under water aspirator vacuum to leave an oily residue. The oily residue was titurated with 100 milliliters of petroleum ether and then the petroleum ether was removed with a water aspirator. The oily residue was vacuum dried in 3 minutes. The white mass was broken up and washed with additional petroleum ether, filtered and vacuum dried. Yield of the white product, N-acetyl-D,L-phenylalanine methyl ester, was 75%. The melting point was 62°-64°. The proton NMR and infrared spectra agreed with the conclusion that the methyl ester of N-acetyl-D,L-phenylalanine was prepared.

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