m-Chloroperbenzoic acid → HCID 69521765, compound

HRID 856552Notes

Reaction equation

HRID 856552 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]([CH2:45][CH:46]6[CH2:49][CH2:48][CH2:47]6)[CH:42]=[CH:43][N:44]=5)=[CH:34][CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:59])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]([CH2:45][CH:46]6[CH2:49][CH2:48][CH2:47]6)[CH:42]=[CH:43][N:44]=5)=[O:59])=[CH:36][CH:37]=4)=[O:30])=[CH:20][C:19]=3[CH:50]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69522507HCID 69522507, compound

Product 1

HCID 69521765HCID 69521765, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[[1-cyclobutylmethylimidazol-2-yl]methyl]sulfanyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (640 mg) in dichloromethane (15 ml) was added dropwise 70% solution of 3-chloroperbenzoic acid (342 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→methanol:ethyl acetate=1:9), to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[[1-cyclobutylmethylimidazol-2-yl]methyl]sulfinyl]phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (439 mg) (Compound 361) 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 (ethyl acetate→methanol:ethyl acetate=1:9)

Sources & evidence

ORD record
ord-04df3dd122c74b1283957898941ff4e2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…