Pyridine → Methyl 2-[(4-chloro-phenyl)sulfonylamino]-3-trifluoromethyl-4,4,4-trifluorobutanoate
Reaction equation
[NH2:1][CH:2]([CH:7]([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])[C:3]([O:5][CH3:6])=[O:4].N1C=CC=CC=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.CCOC(C)=O>C(Cl)Cl>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][CH:2]([CH:7]([C:8]([F:11])([F:10])[F:9])[C:12]([F:13])([F:14])[F:15])[C:3]([O:5][CH3:6])=[O:4])(=[O:31])=[O:30])=[CH:25][CH:24]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of methyl 2-amino-3-(trifluoromethyl)-4,4,4-trifluorobutanoate (2.12 g, 8.87 mmol) in CH2Cl2 (10 mL) was stirred under nitrogen at 25° C. Pyridine (10 mL, 126 mmol) was added dropwise followed by 4-chloro-benzenesulfonyl chloride (2.81 g, 13.3 mmol) in one portion, and the resulting solution stirred for 18 hours at 25° C. After this time period, the reaction was complete by TLC (20:80 EtOAc:PE). After quenching with H2O, the mixture was diluted with Et2O (200 mL). The organic layer was washed with 1 N aq. HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL), and then dried (MgSO4). After concentration, the crude product was purified by Biotage Flash™ 40 chromatography, eluent: 5:95 to 20:80 EtOAc:PE, to obtain methyl 2-[(4-chloro-phenyl)sulfonylamino]-3-trifluoromethyl-4,4,4-trifluorobutanoate as a solid (1.53 g, 42%). Mass Spectrum
Workup
- customAfter quenching with H2O
- additionthe mixture was diluted with Et2O (200 mL)
- washThe organic layer was washed with 1 N aq. HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
- dry with materialdried (MgSO4)
- concentrationAfter concentration
- customthe crude product was purified by Biotage Flash™ 40 chromatography, eluent
Sources & evidence
- ORD record
- ord-8619a39bf831452481443433660dace9
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550629B2
Reaction notes
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