Reaction equation
[Na+].[OH:2][C@H:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][C@H:4]1[C:16]([O-:18])=O.O[N:20]1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[NH4+]>CN(C)C=O>[OH:2][C@H:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][C@H:4]1[C:16]([NH2:20])=[O:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (cis)-4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxylic acid sodium salt (17 g) and 1-hydroxy-7-azabenzotriazole (5 g, 37 mmol) in N,N-dimethylformamide was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (14.1 g, 73.4 mmol), followed by ammonium bicarbonate (21 g, 26.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was then removed under reduced pressure and the residue was treated with aqueous sodium bicarbonate solution. The aqueous phase was extracted with 9:1 dichloromethane:methanol mixture. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a methanol and dichloromethane gradient (0-20% methanol/dichloromethane). This provided the desired compound (9.5 g, 62%).
Workup
- customThe solvent was then removed under reduced pressure
- additionthe residue was treated with aqueous sodium bicarbonate solution
- extractionThe aqueous phase was extracted with 9:1 dichloromethane
- dry with materialThe organic layer was dried (MgSO4)
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-52297c47cb074e87971b38222413d726
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732461B2
Linked notes
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