Glycine methyl ester → N-[1-Oxo-4-(2-pyridinylamino)butyl]glycine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O.C[O:15][C:16](=[O:19])[CH2:17][NH2:18].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][C:11]([NH:18][CH2:17][C:16]([OH:19])=[O:15])=[O:13]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-34affc0ea9694d07b6c2264f9d45bf21
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576637B1
Reaction notes
Loading…