Methanol → Methyl 3-amino-3-(3-nitrophenyl)propanoate

참여 물질

반응 단계

(R)-3-amino-3-(3-nitrophenyl)propionic acid is esterified in analogy to Example 2 by activation with thionyl chloride and reaction with methanol under standard conditions to give methyl 3-amino-3-(3-nitrophenyl)propionate, which is reacted with BOC-Gly-OH and 4-(4-methylpyridin-2-ylamino)butyric acid. Cleavage of the ester results in (R)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid. Use of an excess of NaOH results in the sodium salt of (R)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid. Preparative HPLC results in (R)-3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(3-nitrophenyl)propionic acid trifluoroacetate, RT* 16.89 min, FAB-MS (M+H)+ 444.

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