Sodium Thiosulfate → HCID 136026903, compound

HRID 1673787Notes

Reaction equation

HRID 1673787 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH2:11][CH3:12])[N:8]([CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:7](=[O:20])[C:6]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[NH:38][C:37](=[O:39])[O:36][N:35]=2)=[CH:24][CH:23]=1)[CH2:2][CH2:3][CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:1]([C:5]1[N:10]=[C:9]([CH2:11][CH3:12])[N:8]([CH2:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[C:7](=[O:20])[C:6]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[NH:38][C:37](=[O:39])[O:36][N:35]=2)=[CH:24][CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 136026902HCID 136026902, compound

Product 1

HCID 136026903HCID 136026903, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Butyl-2-ethyl-3-(2-hydroxy-3,3-dimethylbutyl)-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}pyrimidin-4(3H)-one (2.9 g) was dissolved in dichloromethane (60 mL), 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.8 g) was added, and the mixture was stirred for 1 hr. A saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate 5 hydrate were added, and the mixture was further stirred for 1 hr. The reaction mixture was extracted with ethyl acetate, washed 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 (2.9 g, 100%) as a solid.

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b19f558516d495bbf1ff6b1d3ce1192
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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