Glycine methyl ester → N-[1-Oxo-4-(2-pyridinylamino)butyl]glycine

Participants

Reaction Steps

0.364 g of [4-(pyridin-2-ylamino)butyrylamino]acetic acid [obtained from peptide coupling of 4-(pyridin-2-ylamino)butyric acid with glycine methyl ester in the presence of HOBT/TBTU and subsequent hydrolysis of the methyl ester, in each case under standard conditions] is dissolved in 30 ml of DMF, and 0.3 g of methyl 3-amino-3-(4-trifluoromethoxyphenyl)propionate is added, and the mixture is cooled to −30°. Addition of 0.321 g of TBTU and 0.045 g of HOBT is followed by neutralization with 0.22 ml of N-methylmorpholine (NMM). The reaction mixture is stirred at room temperature for 2 days. After removal of the solvent by distillation, the residue is taken up in ethyl acetate, washed with NaHCO3 and saturated NaCl solution and further worked up as usual. Methyl 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(4-trifluoromethoxyphenyl)propionate is obtained, FAB-MS (M+H)+ 497.

Provenance & Evidence