1,2-Dichloroethane → 3-[1-(4-Amino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-propionic acid methyl ester
Reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH2:5][CH2:4][NH:3]1.[CH2:13](ON)[C:14]1[CH:19]=CC=C[CH:15]=1.Cl.C([N:26]([CH:28]([CH3:30])[CH3:29])C)(C)C.[CH2:31](Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:31][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:7]1[C:2](=[O:1])[N:3]([CH2:19][C:14]2[CH:15]=[CH:29][C:28]([NH2:26])=[CH:30][CH:13]=2)[CH2:4][CH2:5][CH:6]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
3-(2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid (g) was dissolved in 0.5 ml of DMF solution. Then BnONH2.HCl (30 mg, 0.188 mmol), diisopropyl methylamine (0.033 ml, 0.189 mmol), EDC (43 mg, 0.224 mmol) and DMAP (5 mg, 0.041 mmol) were added thereto and the mixture was stirred for overnight at room temperature. The mixture was diluted with 7 ml of ethyl acetate and washed with 5% HCl (1 ml) and saturated NaHCO3 solutions (1 ml). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant to give 126 mg (yield: 55%) of the title compound (h).
Workup
- washwashed with 5% HCl (1 ml) and saturated NaHCO3 solutions (1 ml)
- dry with materialThe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant
Sources & evidence
- ORD record
- ord-ff7273d40ff3414185f1f3bace15d23d
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846963B2
Reaction notes
Loading…