Sodium Thiosulfate → HCID 69522774, compound

HRID 856574Notes

Reaction equation

HRID 856574 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH2:24][CH2:25][N:26]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:27]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:36][CH:35]=5)=[CH:30][C:28]=4[CH:29]=3)=[O:22])=[CH:16][CH:15]=2)=[CH:10][N:9]=[CH:8]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:60])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[CH2:24][CH2:25][N:26]([CH2:48][CH:49]([CH3:50])[CH3:51])[C:27]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:36][CH:35]=5)=[CH:30][C:28]=4[CH:29]=3)=[O:22])=[CH:18][CH:19]=2)=[O:60])=[CH:10][N:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 69522500HCID 69522500, compound

Product 1

HCID 69522774HCID 69522774, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of [5-[[[4-[[[7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepin-4-yl]carbonyl]amino]phenyl]thio]methyl]-1H-imidazol-1-yl]ethyl acetate (200 mg) in dichloromethane (10 ml) was added a solution of 3-chloroperbenzoic acid (70%, 0.11 g) in dichloromethane (10 ml) at −78° C. The mixture was stirred for 1 hour at −78° C., an aqueous solution of sodium thiosulfate was added to the mixture, and the mixture was stirred at room temperature for 10 minutes. The mixture was extracted with ethyl acetate, and the organic layer was washed with an aqueous solution of sodium bicarbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (basic silica get, ethyl acetate:hexane 4:1→9:1), to give [5-[[[4-[[[7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepin-4-yl]carbonyl]amino]phenyl]sulfinyl]methyl]-1H-imidazol-1-yl]ethyl acetate (Preparation of Compound 427) (117.6 mg) as yellow amorphous.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with an aqueous solution of sodium bicarbonate and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was separated
  7. custompurified by column chromatography (basic silica get, ethyl acetate:hexane 4:1→9:1)

Sources & evidence

ORD record
ord-e6cba90822314c2b98a70dbdbbc886cb
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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