4-tert-Butylbenzoyl chloride → 2-(4-Tert-butylbenzoylamino)-5-(tert-butyldimethylsilyloxy)-n-(4-methoxyphenyl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].[C:27]([C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[C:27]([C:31]1[CH:32]=[CH:33][C:34]([C:35]([NH:1][C:2]2[CH:18]=[CH:17][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:15][C:3]=2[C:4]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)=[O:5])=[O:36])=[CH:38][CH:39]=1)([CH3:30])([CH3:28])[CH3:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Using the procedure described in Example 68, Part A, 2-amino-5-(tert-butyldimethylsilyloxy)-N-(4-methoxyphenyl)benzamide (460 mg, 1.23 mmol) was reacted with 4-tert-butylbenzoyl chloride (0.243 mL, 1.24 mmol) in N,N-dimethylformamide (10 mL). After quenching the reaction with saturated aqueous sodium carbonate, the resulting precipitate was filtered and washed with 2:1 diethyl ether/hexane. The solid was vacuum dried at 85° C./0.1 mm for 14 h to give 553 mg (84%) of the title compound as a white solid; mp 207° C.
Workup
- customAfter quenching
- customthe reaction with saturated aqueous sodium carbonate
- filtrationthe resulting precipitate was filtered
- washwashed with 2:1 diethyl ether/hexane
- customdried at 85° C./0.1 mm for 14 h
Sources & evidence
- ORD record
- ord-4d237a362f5049d389c81133e33a94ca
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605626B2
Reaction notes
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