Dichloromethane methanol → HCID 90041879, compound

HRID 929153Notes

Reaction equation

HRID 929153 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:9]=[C:10]2[NH:28][C:27]([O:29][C@@H:30]3[CH2:34][O:33][C@@H:32]4[C@:35]([CH:39]=C)([OH:38])[CH2:36][O:37][C@H:31]34)=[N:26][C:11]2=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C[OH:42].C(Cl)Cl>C(#N)C.O.CCOC(C)=O.CO.O.[Ru](Cl)(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]2[NH:28][C:27]([O:29][C@@H:30]3[CH2:34][O:33][C@@H:32]4[C@@:35]([OH:38])([CH:39]=[O:42])[CH2:36][O:37][C@H:31]34)=[N:26][C:11]2=[N:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 3

HCID 21226129Dichloromethane methanolHCID 23667635Sodium periodateHCID 90042151HCID 90042151, compound

Product 1

HCID 90041879HCID 90041879, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Sodium periodate (21.9 mg, 0.102 mmol) was added to a stirred suspension of (3R,3aR,6R,6aS)-3-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-6-vinyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol (23.4 mg, 0.049 mmol) and ruthenium(III) chloride hydrate (1.0 mg, 4.44 μmol) in acetonitrile (0.42 ml) and water (0.07 ml). The reaction mixture was stirred at room temperature for 4 h, then partitioned between EtOAc (20 ml) and saturated aqueous sodium thiosulfate (20 ml). The aqueous layer was extracted with EtOAc (2×20 ml). The organic layers were combined, washed with brine (1×10 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a colorless residue. The residue was dissolved in EtOAc/MeOH and loaded onto a 500 micron 20 cm×20 cm silica gel plate, which was developed twice using 5% MeOH/DCM. The silica containing the product band was collected and eluted with 10% MeOH/DCM (80 ml). The solvent was evaporated under reduced pressure to give the title compound as a colorless residue. LC-MS: calculated for C25H20ClN3O5 477.11 observed m/e: 478.05 (M+H)+ (Rt 1.15/2 min)

Workup

  1. custompartitioned between EtOAc (20 ml) and saturated aqueous sodium thiosulfate (20 ml)
  2. extractionThe aqueous layer was extracted with EtOAc (2×20 ml)
  3. washwashed with brine (1×10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a colorless residue
  8. customThe silica containing the product band was collected
  9. washeluted with 10% MeOH/DCM (80 ml)
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-19d3c5ee419b49cba763ebab1908e407
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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