Acetone → (S)-N-methyl-N-(2-phenyl-4-oxobutyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

HRID 1584500Notes

Reaction equation

HRID 1584500 reaction equation
[CH3:1][N:2]([CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][CH:21]=C)[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C@H:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16].CC(C)=[O:31].C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+]>ClCCl.[Os](=O)(=O)(=O)=O.CO.ClCCl.O1CCCC1.O.O.C(O)(C)(C)C>[CH3:1][N:2]([CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][CH:21]=[O:31])[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C@H:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16]

Participants

11

Reactant 4

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 69775799(S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

Product 1

HCID 86754360(S)-N-methyl-N-(2-phenyl-4-oxobutyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

Reagents, catalysts & solvents 6

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 21226129Dichloromethane methanolSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide (1.03 g, 2.74 mmol), acetone (15 mL, t-butanol (7.5 mL), water (7.5 mL), and a solution of N-methylmorpholine N-oxide (0.74 mL, 50% in water, 3.56 mmol). Add a solution of osmium tetraoxide (1.0 mL, 4% in water). After 36 hours, evaporate in vacuo to remove most of the acetone and extract the evaporated reaction mixture with dichloromethane. Extract the organic layer with an aqueous 10% solution of sodium thiosulfate. Extract the aqueous layer five times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Combine the residue and tetrahydrofuran/water (20 mL, 4/1). Add sodium meta-periodate (0.7 g, 3.29 mmol). After 25 minutes, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to obtain a residue. Dilute the residue with dichloromethane (100 mL), extract with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% methanol/dichloromethane to give the title compound.

Workup

  1. customevaporate in vacuo
  2. customto remove most of the acetone
  3. extractionextract
  4. customthe evaporated reaction mixture with dichloromethane
  5. extractionExtract the organic layer with an aqueous 10% solution of sodium thiosulfate
  6. extractionExtract the aqueous layer five times with dichloromethane
  7. dry with materialDry the combined organic layers over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue
  11. waitAfter 25 minutes
  12. filtrationfilter the reaction mixture
  13. washrinse the solids with tetrahydrofuran
  14. customevaporate the filtrate
  15. customto obtain a residue
  16. extractionextract with water
  17. dry with materialdry over MgSO4
  18. filtrationfilter
  19. customevaporate in vacuo
  20. customto give a residue

Sources & evidence

ORD record
ord-3dda7f8144f24073bbd0b91704cfe839
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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