Methyl morpholine oxide → HCID 21311278, compound

HRID 429486Notes

Reaction equation

HRID 429486 reaction equation
[CH3:1][N:2]([CH2:18][C@H: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]([N: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(O)(C)(C)C.O.C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+]>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O.CO.ClCCl.O1CCCC1.O>[CH3:1][N:2]([CH2:18][C@H: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]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[O:15][CH3:16]

Participants

9

Reactant 4

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 54455874HCID 54455874, compoundHCID 86602953Acetone tBuOH Water

Product 1

HCID 21311278HCID 21311278, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (3.13 g, 8.3 mmol), acetone/t-butanol/water (2/1/1, 90 mL), and a solution of N-methylmorpholine N-oxide (2.06 mL, 50% in water, 9.95 mmol). Add a solution of osmium tetraoxide (2.56 mL, 4% in water, 0.5 mmol). After 18 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. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue: Rf=0.22 (silica gel, 7% methanol/dichloromethane/0.1% concentrated ammonium hydroxide). Combine the residue (3.6 g, 8.3 mmol) and tetrahydrofuran/water (90 mL, 4/1). Add sodium meta-periodate (2.13 g, 9.95 mmol). After 1 hour, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to obtain a residue. Dilute the residue with ethyl acetate (150 mL), extract with brine, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane/0.1% concentrated ammonium hydroxide to give the title compound: Rf=0.33 (silica gel, 7% methanol/dichloromethane/0.1% concentrated ammonium hydroxide). [α]2D0=13.70° (c=0.59, chloroform)

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. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue
  10. waitAfter 1 hour
  11. filtrationfilter the reaction mixture
  12. washrinse the solids with tetrahydrofuran
  13. customevaporate the filtrate
  14. customto obtain a residue
  15. extractionextract with brine
  16. dry with materialdry over MgSO4
  17. filtrationfilter
  18. customevaporate in vacuo
  19. customto give a residue

Sources & evidence

ORD record
ord-3998d4b6bc094529aec2b4eb380f1783
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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