Sodium Thiosulfate → HCID 10509052, compound

HRID 1422063Notes

Reaction equation

HRID 1422063 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:31]([C:33]2[O:34][C:35]3[CH:41]=[CH:40][C:39]([C:42]([NH:44][CH2:45][CH3:46])=[O:43])=[CH:38][C:36]=3[N:37]=2)[OH:32])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[C:15]([C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([C:31]([C:33]2[O:34][C:35]3[CH:41]=[CH:40][C:39]([C:42]([NH:44][CH2:45][CH3:46])=[O:43])=[CH:38][C:36]=3[N:37]=2)=[O:32])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:21])[C:15]([C:47]2[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 10628651HCID 10628651, compound

Product 1

HCID 10509052HCID 10509052, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the objective compound (448 mg, 0.623 mmol) of Step (2) in DMSO (5 mL) was added Dess-Martin periodinane (446 mg, 1.05 mmol) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution (5 mL) containing sodium thiosulfate in a concentration of 0.22 g/mL, and the mixture was stirred at room temperature and extracted with ethyl acetate. The insoluble material in the extract was collected by filtration and the filtrate was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue and the insoluble material obtained earlier were combined, and separated and purified by silica gel column chromatography (50:1 chloroform:methanol) to give the title compound as pale-yellow crystals (268 mg, 60%).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. extractionextracted with ethyl acetate
  3. filtrationThe insoluble material in the extract was collected by filtration
  4. washthe filtrate was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue and the insoluble material obtained earlier
  8. customseparated
  9. custompurified by silica gel column chromatography (50:1 chloroform:methanol)

Sources & evidence

ORD record
ord-93478ccb11ad4e749797f69ea3a56477
Source dataset
uspto-grants-2000_06
Patent number
US06080738

Reaction notes

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