Sodium Thiosulfate → HCID 53931671, compound

HRID 429489Notes

Reaction equation

HRID 429489 reaction equation
[CH3:1][N:2]([CH2:17][C@H:18]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)[CH2:19][CH:20]=C)[C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1.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.CO.ClCCl.O1CCCC1.O.CC(C)=O.C(O)(C)(C)C.O>[CH3:1][N:2]([CH2:17][C@H:18]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)[CH2:19][CH:20]=[O:34])[C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1

Participants

9

Reactant 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 57227893HCID 57227893, compound

Product 1

HCID 53931671HCID 53931671, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 21226129Dichloromethane methanolSolvent2×HCID 21881883Oxolane--water (1/1)SolventHCID 86602953Acetone tBuOH WaterSolvent

Procedure

Combine (S)-N-methyl-N-(2-(3,4-dichlorophenyl)pent-4-enyl)-3,4,5-trimethoxybenzamide (1.39 g, 3.17 mmol), acetone/t-butanol/water (2/1/1, 32 mL), and a solution of N-methylmorpholine N-oxide (0.89 g 50% in water, 1.2). Add a solution of osmium tetraoxide (1.2 g, 4% in water, 0.06 mmol). After 2 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 layers, extract the organic layer with brine, dry over MgSO4, filter, and evaporate in vacuo to give a residue: Rf=0.26 (sliica gel, 6% methanol/dichloromethane). Combine the residue and tetrahydrofuran/water (4/1 40 mL). Add sodium meta-periodate (0.81 g, 3.8 mmol). After 1.5 hours, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to remove most of the tetrahydrofuran. Dilute the evaporated reaction mixture with dichlromethane. Extract with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1% methanol/dichloromethane to 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 layers
  6. extractionextract the organic layer with brine
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue
  11. waitAfter 1.5 hours
  12. filtrationfilter the reaction mixture
  13. washrinse the solids with tetrahydrofuran
  14. customevaporate the filtrate
  15. customto remove most of the tetrahydrofuran
  16. additionDilute
  17. customthe evaporated reaction mixture with dichlromethane
  18. extractionExtract with water
  19. dry with materialdry over MgSO4
  20. filtrationfilter
  21. customevaporate in vacuo
  22. customto give a residue

Sources & evidence

ORD record
ord-3e6a89a012384a55acf4302c06eb066a
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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