Sodium Thiosulfate → HCID 54538205, compound

HRID 429479Notes

Reaction equation

HRID 429479 reaction equation
[CH3:1][N:2]([CH2:18][C@H:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:20][CH:21]=C)[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16].C[N+]1([O-])CC[O:34]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.C(OCC)(=O)C.O.O1CCCC1.CC(C)=O.C(O)(C)(C)C.O>[CH3:1][N:2]([CH2:18][C@H:19]([C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)[CH2:20][CH:21]=[O:34])[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16]

Participants

10

Reactant 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 53841613HCID 53841613, compound

Product 1

HCID 54538205HCID 54538205, compound

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 86602953Acetone tBuOH WaterSolvent

Procedure

Combine (S)-N-methyl-N-(2-(4-fluorophenyl)pent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (4.46 g, 11.3 mmol), acetone/t-butanol/water (2/1/1, 64 mL), and a solution of N-methylmorpholine N-oxide (3.0 mL, 50% in water, 14.5 mmol). Add a solution of osmium tetraoxide (3.0 mL, 4% in water, 0.5 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 (80 mL), and water (20 mL). Add sodium meta-periodate (3.63 g). After 1.5 hours, filter the reaction mixture, rinse the solids with dichloromethane, and evaporate the filtrate to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.22 (silica gel, ethyl acetate).

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
  14. customto obtain a residue

Sources & evidence

ORD record
ord-a4b0d0db0a044e82874b5610023af22e
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

Loading…