Sodium Thiosulfate → HCID 54052220, compound

HRID 429498Notes

Reaction equation

HRID 429498 reaction equation
[CH3:1][N:2]([CH2:22][C@H:23]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:24][CH:25]=C)[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[C:14]([C:15]([F:18])([F:17])[F:16])=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].C[N+]1([O-])CC[O:38]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O.O1CCCC1.CC(C)=O.C(O)(C)(C)C.O>[CH3:1][N:2]([CH2:22][C@H:23]([C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)[CH2:24][CH:25]=[O:38])[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[C:14]([C:15]([F:16])([F:18])[F:17])=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20]

Participants

9

Reactant 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 54566063HCID 54566063, compound

Product 1

HCID 54052220HCID 54052220, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 86602953Acetone tBuOH WaterSolvent

Procedure

Combine (S)-N-methyl-N-(2-(4-fluorophenyl)pent-4-enyl)-2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)benzamide (10 mmol), acetone/t-butanol/water (2/1/1, 56 mL), and a solution of N-methylmorpholine N-oxide (2.6 mL, 50% in water, 12.7 mmol). Add a solution of osmium tetraoxide (2.6 mL, 4% in water, 0.44 mmol). After 3 hours, evaporate in vacuo to remove most of the acetone and partition the evaporated reaction mixture between dichloromethane and an aqueous 10% solution of sodium thiosulfate. Separate the layer, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue, tetrahydrofuran (70 mL), and water (17.5 mL). Add sodium meta-periodate (3.2 g). After 1.5 hours, filter the reaction mixture, rinse the solids with dichloromethane, and evaporate the filtrate give the title compound.

Workup

  1. customevaporate in vacuo
  2. customto remove most of the acetone
  3. custompartition
  4. customthe evaporated reaction mixture between dichloromethane
  5. customSeparate the layer
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue
  10. waitAfter 1.5 hours
  11. filtrationfilter the reaction mixture
  12. washrinse the solids with dichloromethane
  13. customevaporate the filtrate

Sources & evidence

ORD record
ord-74c275da6f2340f7aa34d1a726509f26
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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