m-Chloroperbenzoic acid → HCID 3013579, compound

HRID 856562Notes

Reaction equation

HRID 856562 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38][CH2:39][C:40]5[N:41]=[CH:42][N:43]([CH2:45][CH2:46][CH3:47])[CH:44]=5)=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:48]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:57])C=1>ClCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:33]=[CH:34][C:35]([S:38]([CH2:39][C:40]5[N:41]=[CH:42][N:43]([CH2:45][CH2:46][CH3:47])[CH:44]=5)=[O:57])=[CH:36][CH:37]=4)=[O:30])=[CH:20][C:19]=3[CH:48]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69522647HCID 69522647, compound

Product 1

HCID 3013579HCID 3013579, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propylimidazol-4-yl]methyl]sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (140 mg) in dichloromethane (15 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (78 mg) in dichloromethane (15 ml) at −78° C. The reaction vessel was removed from a dry ice-acetone bath, and an aqueous solution of sodium thiosulfate was added to the reaction vessel with strongly stirring. The mixture was allowed to be at room temperature, stirred for 30 minutes, and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (methanol-ethyl acetate=1:9), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propylimidazol-4-yl]methyl]sulfinyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (103 mg) (Compound 394) as yellow amorphous.

Workup

  1. customThe reaction vessel was removed from a dry ice-acetone bath
  2. additionan aqueous solution of sodium thiosulfate was added to the reaction vessel
  3. customto be at room temperature
  4. stirringstirred for 30 minutes
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate, and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe obtained residue was separated
  10. custompurified by silica gel column chromatography (methanol-ethyl acetate=1:9)

Sources & evidence

ORD record
ord-afecbda846cf47d18953707e0dc60696
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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