Dimethyl Sulfoxide → Biphenyl-2-ylcarbamic acid 1-{2-[(4-formyl-2-methoxybenzoyl)methylamino]ethyl}piperidin-4-yl Ester
Reaction equation
[OH:1][CH2:2][C:3]1[CH:36]=[CH:35][C:6]([C:7]([CH2:9][NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20](=[O:34])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:15][CH2:14]2)=[O:8])=[C:5]([O:37][CH3:38])[CH:4]=1.CS(C)=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:2]([C:3]1[CH:36]=[CH:35][C:6]([C:7]([CH2:9][NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20](=[O:34])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:15][CH2:14]2)=[O:8])=[C:5]([O:37][CH3:38])[CH:4]=1)=[O:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of biphenyl-2-ylcarbamic acid 1-{2-[(4-hydroxymethyl-2-methoxybenzoyl)methylamino]ethyl}piperidin-4-yl ester (78 mg, 1.5 mmol; prepared as described in Preparation 20) in DCM (2.5 mL) at −15° C. was added DMSO (130 μL, 22.5 mmol), and DIPEA (130 μL, 7.5 mmol). To the solution was added sulfur trioxide-pyridine complex (240 mg, 15 mmol). After 30 minutes, the reaction mixture was quenched with water (˜3 mL). Two layers were separated, the organic layer was dried over MgSO4; filtered and the title intermediate was used directly in the next reaction.
Workup
- additionTo the solution was added sulfur trioxide-pyridine complex (240 mg, 15 mmol)
- customthe reaction mixture was quenched with water (˜3 mL)
- customTwo layers were separated
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- customthe title intermediate was used directly in the next reaction
Sources & evidence
- ORD record
- ord-4d4de4c63c2e41409f2644d6aa41b2b7
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013152B2
Reaction notes
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