Water → HCID 68617701, compound

HRID 2233763Notes

Reaction equation

HRID 2233763 reaction equation
[OH:1]OS([O-])=O.[K+].[CH2:7]([S:9][C:10]1[CH:30]=[CH:29][C:13]([O:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([F:27])([F:26])[F:25])[CH:22]=3)[NH:17][C:16]=2[CH3:28])=[CH:12][CH:11]=1)[CH3:8].[OH2:31]>C(#N)C>[CH2:7]([S:9]([C:10]1[CH:30]=[CH:29][C:13]([O:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[CH:22]=3)[NH:17][C:16]=2[CH3:28])=[CH:12][CH:11]=1)(=[O:1])=[O:31])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfite2×HCID 68616388HCID 68616388, compound

Product 1

HCID 68617701HCID 68617701, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of oxone (1.0 g) in water (30 ml) was added to a solution of the product from step (ii) (1.4 g) in acetonitrile (100 ml) and stirred for 2 h. Further oxone (500 mg) was added and the reaction stirred for a further 3 h. The mixture was evaporated to ˜50 ml, extracted with EtOAc, washed with aqueous sodium metabisulphite and brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with 30% etlhylacetate/iso-hexane.

Workup

  1. stirringthe reaction stirred for a further 3 h
  2. customThe mixture was evaporated to ˜50 ml
  3. extractionextracted with EtOAc
  4. washwashed with aqueous sodium metabisulphite and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica eluting with 30%

Sources & evidence

ORD record
ord-96b533d0b27b4f1aa0f2de275d14da7c
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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