m-Chloroperbenzoic acid → tert-Butyl ((3R)-1-(3-(methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indole-6-carbonyl)pyrrolidin-3-yl)carbamate
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:29][CH2:28][C@@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26]3)=[O:24])=[CH:20][CH:21]=2)[N:16]([C:38]2[N:43]=[CH:42][C:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:40][N:39]=2)[CH:15]=1>C1COCC1.C(OCC)(=O)C>[CH3:12][S:13]([C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:29][CH2:28][C@@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35])[CH2:26]3)=[O:24])=[CH:20][CH:21]=2)[N:16]([C:38]2[N:39]=[CH:40][C:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:42][N:43]=2)[CH:15]=1)=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
m-Chloroperoxybenzoic acid (77%, 0.20 g, 0.92 mmol) in THF (5 mL) was added to an ice-cooled solution of 223c) (0.54 g, 1.02 mmol) in THF (100 mL) and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was then diluted with ethyl acetate (50 mL) and successively washed with saturated sodium hydrogen carbonate solution (2×50 mL) and brine (1×50 mL). The organic phase was dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography [silica gel; dichloromethane with 2% methanol]. White solid. Yield: 0.28 g (51% of theory)
Workup
- washsuccessively washed with saturated sodium hydrogen carbonate solution (2×50 mL) and brine (1×50 mL)
- dry with materialThe organic phase was dried over sodium sulfate
- customevaporated
- customThe residue was purified by flash column chromatography [silica gel; dichloromethane with 2% methanol]
Sources & evidence
- ORD record
- ord-8641bcd536694c29a1c8959c407232fb
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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