Sodium periodate → HCID 54306004, compound

HRID 1859356Notes

Reaction equation

HRID 1859356 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[CH:10]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[N:11]([CH2:23][CH2:24][CH2:25][OH:26])[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:35].[Na+]>C(#N)C.C(Cl)(Cl)(Cl)Cl.O.O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([CH:10]([N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH2:23][CH2:24][C:25]([OH:35])=[O:26])[CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 54387880HCID 54387880, compound

Product 1

HCID 54306004HCID 54306004, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

Cyclohexyl[(3-hydroxypropyl)(4-methoxybenzenesulfonyl)amino]acetic acid benzyl ester (45.8 grams, 96 mmol) and sodium periodate (92.6 grams, 433 mmol) were dissolved in a mixture of acetonitrile (345 mL), carbon tetrachloride (345 mL) and water 460 mL). While cooling in an ice bath, ruthenium trichloride monohydrate (4.4 grams, 21 mmol) was then added. The resulting mixture was mechanically stirred with ice bath cooling for 30 minutes. The bath was removed and stirring was continued at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate and filtered through diatomaceous earth. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine. After drying over magnesium sulfate, the solvents were evaporated to give a dark oil from which 3-[(benzyloxycarbonylcyclohexylmethyl)-(4-methoxybenzenesulfonyl) amino]propionic acid, a white foam (28.1 grams, 60%), was isolated by flash chromatography on silica gel eluting sequentially with chloroform and 1% methanol in chloroform.

Workup

  1. temperatureWhile cooling in an ice bath
  2. temperaturecooling for 30 minutes
  3. customThe bath was removed
  4. stirringstirring
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. filtrationfiltered through diatomaceous earth
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe combined organic layers were washed with water and saturated brine
  10. dry with materialAfter drying over magnesium sulfate
  11. customthe solvents were evaporated

Sources & evidence

ORD record
ord-f78afcd4758e4d3585b9f7a6b23911f5
Source dataset
uspto-grants-2000_11
Patent number
US06153609

Reaction notes

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