Reaction equation
[Si:1]([O:8][NH2:9])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([S:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]3[C:32](O)=[O:33])(=[O:25])=[O:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>C(Cl)Cl>[O:8]([NH:9][C:32]([CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][N:26]1[S:23]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=2)[CH2:18][CH2:19]1)(=[O:25])=[O:24])=[O:33])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
O-(tert-butyldimethylsilyl)hydroxylamine (57 mg, 0.39 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (59 mg, 0.31 mmol) were added to a solution of 1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxylic acid (100 mg, 0.26 mmol), [prepared as described above] in methylene chloride (4 ml). The reaction mixture was stirred overnight at RT and then diluted with methylene chloride. The solution was washed with water, 10% citric acid, and brine, and dried over MgSO4. After the organics were removed the residue was chromatographed (SiO2, 2030% ethyl acetate/hexane) to give N-tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(RS)-carboxamide as a colorless foam (56%).
Workup
- washThe solution was washed with water, 10% citric acid, and brine
- dry with materialdried over MgSO4
- customAfter the organics were removed the residue
- customwas chromatographed (SiO2, 2030% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-3f6f692b0648401ead69ecc96721e7bf
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130220
Linked notes
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