Sodium Thiosulfate → HCID 69521405, compound

HRID 856571Notes

Reaction equation

HRID 856571 reaction equation
[NH2:1][C:2](=[O:51])[CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH2:23][CH2:24][N:25]([CH2:47][CH:48]([CH3:50])[CH3:49])[C:26]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:35][CH:34]=4)=[CH:29][C:27]=3[CH:28]=2)=[O:21])=[CH:15][CH:14]=1.ClC1C=CC=C(C(OO)=[O:60])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[NH2:1][C:2](=[O:51])[CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][S:12]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH2:23][CH2:24][N:25]([CH2:47][CH:48]([CH3:50])[CH3:49])[C:26]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:35][CH:34]=4)=[CH:29][C:27]=3[CH:28]=2)=[O:21])=[CH:15][CH:14]=1)=[O:60]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 69521950HCID 69521950, compound

Product 1

HCID 69521405HCID 69521405, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-[4-[[[1-(4-amino-4-oxobutyl)-1H-imidazol-2-yl]methyl]thio]phenyl]-7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (350 mg) in dichloromethane (30 ml) was added dropwise a solution of 3-chloroperbenzoic acid (70%, 0.18 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 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 gel, ethanol:ethyl acetate 1:19→1:9), to give N-[4-[[[1-(4-amino-4-oxobutyl)-1H-imidazol-2-yl]methyl]sulfinyl]phenyl]-7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 416) (259.9 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 gel, ethanol:ethyl acetate 1:19→1:9)

Sources & evidence

ORD record
ord-f587e521bb6842a9b3e6044177e68683
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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