m-Chloroperbenzoic acid → HCID 66670351, compound

HRID 1514657Notes

Reaction equation

HRID 1514657 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([NH:22][CH2:23][C:24]2([N:30]([CH3:32])[CH3:31])[CH2:29][CH2:28][S:27][CH2:26][CH2:25]2)=[O:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)(Cl)Cl>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:8]([CH3:19])=[C:7]([C:20]([NH:22][CH2:23][C:24]2([N:30]([CH3:32])[CH3:31])[CH2:25][CH2:26][S:27](=[O:41])[CH2:28][CH2:29]2)=[O:21])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 66670229HCID 66670229, compound

Product 1

HCID 66670351HCID 66670351, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 400 mg portion of 5-tert-butyl-N-{[4-(dimethylamino)tetrahydro-2H-thiopyran-4-yl]methyl}-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide was dissolved in 4 ml of chloroform and, under ice-cooling, 210 mg of 3-chloroperbenzoic acid was added, followed by stirring under ice-cooling for 1 hour. Then, 100 mg of 3-chloroperbenzoic acid was added, followed by stirring for 30 minutes. A 10% sodium hydrogen sulfite aqueous solution and a saturated sodium bicarbonate aqueous solution to the reaction solution, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol:hexane=1:0:0-100:1:0-50:1:0-30:1:0) to obtain 213 mg of 5-tert-butyl-N-{[4-(dimethylamino)-1-oxidotetrahydro-2H-thiopyran-4-yl]methyl}-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide as a colorless oil. This product was dissolved in 2.5 ml of acetonitrile at 80° C., 44 mg of oxalic acid was added, followed by stirring at the same temperature for 10 minutes and then stirring at room temperature for 2 hours. The resulting solid was collected by filtration and then washed with acetonitrile to obtain 199 mg of 5-tert-butyl-N-{[4-(dimethylamino)-1-oxidotetrahydro-2H-thiopyran-4-yl]methyl}-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide oxalate as a colorless solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. stirringby stirring for 30 minutes
  4. extractionA 10% sodium hydrogen sulfite aqueous solution and a saturated sodium bicarbonate aqueous solution to the reaction solution, followed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporation of the solvent under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol:hexane=1:0:0-100:1:0-50:1:0-30:1:0)

Sources & evidence

ORD record
ord-2d622ed9634b4a9ba71158e3f82c1c9a
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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