Sodium Thiosulfate Pentahydrate → HCID 136146677, compound

HRID 1673928Notes

Reaction equation

HRID 1673928 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:26])[N:11]([CH2:19][CH:20]([OH:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:12]([CH3:18])=[N:13][C:14]=1[CH2:15][CH2:16][CH3:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:23][C:21]([CH3:22])([CH3:24])[C:20](=[O:25])[CH2:19][N:11]1[C:10](=[O:26])[C:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][C:36](=[O:38])[O:35][N:34]=3)=[CH:3][C:2]=2[F:1])=[C:14]([CH2:15][CH2:16][CH3:17])[N:13]=[C:12]1[CH3:18]

Participants

7

Reactant 4

HCID 61475Sodium Thiosulfate PentahydrateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 136146700HCID 136146700, compound

Product 1

HCID 136146677HCID 136146677, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-{[3-fluoro-2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-3-(2-hydroxy-3,3-dimethylbutyl)-2-methyl-6-propylpyrimidin-4(3H)-one (0.28 g), 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (0.34 g) and methylene chloride (15 mL) was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate and sodium thiosulfate pentahydrate were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with chloroform, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.15 g, 53%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. washwashed with water
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-951d65431c144f6e9da5ba14841ba685
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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