Water → HCID 59025536, compound

HRID 1444831Notes

Reaction equation

HRID 1444831 reaction equation
I([O-])(=O)(=O)=O.[Na+].O.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)CC=[C:12]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=1[O:26][CH3:27].F[C:29](F)(F)[C:30]([OH:32])=[O:31]>ClC(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl.C(#N)C>[Cl:8][C:9]1[CH:17]=[CH:16][C:15]([CH2:29][C:30]([OH:32])=[O:31])=[C:11]([CH2:12][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[O:26][CH3:27])[CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 23667635Sodium periodateHCID 59025495HCID 59025495, compound

Product 1

HCID 59025536HCID 59025536, compound

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

701.6 mg of sodium periodate (3.28 mol) and 3.6 mg of ruthenium(III) chloride monohydrate (0.02 mol) are introduced into 3 ml of water. 229.4 mg of the compound from Example 24A (0.80 mol) dissolved in 2 ml of tetrachloromethane are added and, after addition of 2 ml of acetonitrile, the reaction mixture is stirred at room temperature for 16 h. For working up, the mixture is poured into 20 ml of a 5% strength aqueous trifluoroacetic acid solution and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate, and the solvent is removed in a rotary evaporator. The residue is stirred with 5 ml of ethyl acetate and 2 ml of n-heptane and stored at 5° C. for 3 h. The deposited product is filtered off, washed with m-pentane and dried under high vacuum. 119.0 mg (44% of theory) of the title compound are obtained.

Workup

  1. additionare added
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customthe solvent is removed in a rotary evaporator
  5. stirringThe residue is stirred with 5 ml of ethyl acetate and 2 ml of n-heptane
  6. waitstored at 5° C. for 3 h
  7. filtrationThe deposited product is filtered off
  8. washwashed with m-pentane
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-d4acfe09f1914db1a8dd070486357c0e
Source dataset
uspto-grants-2010_02
Patent number
US07662956B2

Reaction notes

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