HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → HCID 131735095, compound

HRID 929205
Notes
Print preview

Reaction equation

HRID 929205 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:9]=[C:10]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:27]([O:37][C@H:38]3[C@H:42]4[O:43][CH2:44][C@@H:45]([O:46][CH2:47][CH:48]=[O:49])[C@H:41]4[O:40][CH2:39]3)=[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.[OH2:50]>C(Cl)(Cl)(Cl)Cl.C(#N)C.CCOC(C)=O.C(Cl)Cl.CO.CC(O)=O.O.[Ru](Cl)(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:27]([O:37][C@H:38]3[C@H:42]4[O:43][CH2:44][C@@H:45]([O:46][CH2:47][C:48]([OH:50])=[O:49])[C@H:41]4[O:40][CH2:39]3)=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 90067176HCID 90067176, compound

Product 1

HCID 131735095HCID 131735095, compound

Reagents, catalysts & solvents 5

HCID 6093376Ruthenium trichloride hydrateCatalyst
HCID 5943
Carbon Tetrachloride
Solvent
HCID 6342AcetonitrileSolvent
HCID 8857Ethyl AcetateSolvent
HCID 21877243DCM MeOH AcOHSolvent

Procedure

Sodium periodate (19.4 mg, 0.091 mmol) and ruthenium (III) chloride hydrate (1.3 mg, 5.77 μmol) were added to a stirred biphasic mixture of 2-[[(3R,3aR,6R,6aR)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]acetaldehyde (13.8 mg, 0.022 mmol) in carbon tetrachloride (0.12 ml), acetonitrile (0.09 ml), and water (0.15 ml). The reaction mixture was stirred at room temperature. After 3 hours, the reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml). The aqueous layer was extracted with EtOAc (2×20 ml). The organic layers were combined, washed with brine (1×20 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a colorless residue. The residue was dissolved in EtOAc and loaded onto a 500 micron 20 cm×20 cm silica gel plate, which was developed twice using a 94:5:1 DCM/MeOH/AcOH solvent mixture (fresh solvent was used for each development). The silica containing the product band was collected and eluted with a 90:9:1 DCM/MeOH/AcOH solvent mixture (80 ml). The solvent was evaporated under reduced pressure to give the desired product as a colorless residue. LC-MS: calculated for C32H36ClN3O7Si 637.2 observed m/e: 638.33 (M+H)+ (Rt 1.35/2 min)

Workup

  1. customthe reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml)
  2. extractionThe aqueous layer was extracted with EtOAc (2×20 ml)
  3. washwashed with brine (1×20 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 a 90:9:1 DCM/MeOH/AcOH solvent mixture (80 ml)
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-373c718d9ca2458abd4e274c380be580
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290517B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes