m-Chloroperbenzoic acid → HCID 69521862, compound

HRID 856554Notes

Reaction equation

HRID 856554 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:45]6[CH2:47][CH2:46]6)[CH:42]=[CH:43][N: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:45]6[CH2:46][CH2:47]6)[CH:42]=[CH:43][N: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 69521334HCID 69521334, compound

Product 1

HCID 69521862HCID 69521862, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[[1-cyclopropylimidazol-2-yl]methyl]sulfanyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (700 mg) in dichloromethane (15 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (389 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 (ethyl acetate), and was recrystallized from hexane-ethyl acetate, to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[[1-cyclopropylimidazol-2-yl]methyl]sulfinyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (526 mg) (Compound 367) as yellow crystals.

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 (ethyl acetate)
  11. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-517d8d978a254b7a93317edac145b0f3
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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