Dichloromethane methanol → HCID 90042613, compound

HRID 929154Notes

Reaction equation

HRID 929154 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([C@:10]1([OH:41])[C@H:14]2[O:15][CH2:16][C@@H:17]([O:18][C:19]3[NH:20][C:21]4[C:22]([N:40]=3)=[N:23][C:24]([C:28]3[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:30][CH:29]=3)=[C:25]([Cl:27])[CH:26]=4)[C@H:13]2[O:12][CH2:11]1)[CH:8]=C.C[OH:43].C(Cl)Cl>C(#N)C.O.CCOC(C)=O.O.[Ru](Cl)(Cl)Cl>[Cl:27][C:25]1[CH:26]=[C:21]2[NH:20][C:19]([O:18][C@@H:17]3[CH2:16][O:15][C@@H:14]4[C@:10]([CH2:7][CH:8]=[O:43])([OH:41])[CH2:11][O:12][C@H:13]34)=[N:40][C:22]2=[N:23][C:24]=1[C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:32][CH:33]=1

Participants

8

Reactant 3

HCID 21226129Dichloromethane methanolHCID 23667635Sodium periodateHCID 90042055HCID 90042055, compound

Product 1

HCID 90042613HCID 90042613, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ruthenium(III) chloride hydrate (3.7 mg, 0.016 mmol) and sodium periodate (121.7 mg, 0.569 mmol) were added to a stirred solution of (3R,3aR,6R,6aS)-6-allyl-3-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol (122.5 mg, 0.250 mmol) in acetonitrile (2.14 ml) and water (0.36 ml). The reaction mixture was stirred at room temperature for 3 h, then partitioned between EtOAc (75 ml) and saturated aqueous sodium thiosulfate (40 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a colorless residue. This material was dissolved in EtOAc and loaded onto three 500 micron 20 cm×20 cm silica gel plates, which were developed using 10% 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 and the resulting residue was lyophilized from ethanol and benzene to give the title compound as a white solid. LC-MS: calculated for C26H22ClN3O5 491.12 observed m/e: 492.18 (M+H)+ (Rt 1.18/2 min).

Workup

  1. custompartitioned between EtOAc (75 ml) and saturated aqueous sodium thiosulfate (40 ml)
  2. extractionThe aqueous layer was extracted with EtOAc (2×50 ml)
  3. washwashed with brine (1×30 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-2c23aa47fcb347bfb4fb35fb445c60e2
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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