Sodium Thiosulfate → HCID 69521589, compound

HRID 856568Notes

Reaction equation

HRID 856568 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH2:24][CH2:25][N:26]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:27]3[CH:33]=[CH:32][C:31]([C:34]4[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]=4)=[CH:30][C:28]=3[CH:29]=2)=[O:22])=[CH:16][CH:15]=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[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]2[CH2:24][CH2:25][N:26]([CH2:48][CH:49]([CH3:50])[CH3:51])[C:27]3[CH:33]=[CH:32][C:31]([C:34]4[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]=4)=[CH:30][C:28]=3[CH:29]=2)=[O:22])=[CH:18][CH:19]=1)=[O:60])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 69521815HCID 69521815, compound

Product 1

HCID 69521589HCID 69521589, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of [2-[[[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 (350 mg) in dichloromethane (10 ml) was added dropwise 3-chloroperbenzoic acid (70%, 146 mg) 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 sodium bicarbonate solution 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 1:1→ethyl acetate→ethanol:ethyl acetate 1:19), to give [2-[[[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 411) (278.7 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 sodium bicarbonate solution 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 1:1→ethyl acetate→ethanol:ethyl acetate 1:19)

Sources & evidence

ORD record
ord-18059bcb9a82410989b5200904495c44
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…