Acetyl chloride → tert-Butyl {2-(acetylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate
Reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.C(N(CC)C(C)C)(C)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl.C(OCC)(=O)C>[C:31]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)(=[O:33])[CH3:32]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Of the compound from Example 22A, 75 mg (0.25 mmol) were introduced in 2.5 ml of dichloromethane together with 60 μl (0.35 mmol) of N,N-diisopropylethylamine and admixed at RT with 21 μl (0.30 mmol) of acetyl chloride. The mixture was stirred at RT for 1 h. The reaction mixture was diluted with ethyl acetate and washed in succession twice each with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and then with saturated aqueous sodium chloride solution, dried over sodium sulphate and freed from the solvent on a rotary evaporator. Further drying in an HV gave 88 mg of the title compound (100% of theory).
Workup
- washwashed in succession twice each with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution
- dry with materialwith saturated aqueous sodium chloride solution, dried over sodium sulphate
- customfreed from the solvent on a rotary evaporator
- customFurther drying in an HV
Sources & evidence
- ORD record
- ord-dc82cc01f719425f882f51edede579f9
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202895B2
Reaction notes
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