Acetonitrile → HCID 178441928, compound

HRID 1656032Notes

Reaction equation

HRID 1656032 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[C:13]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:14][N:15]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:16]=3[CH2:17][OH:18])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[NH:38][N:37]=[N:36][N:35]=1.C[N+]1([O-])CCOCC1.ClCCl.C(#N)C>ClCCl.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[C:13]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:14][N:15]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:16]=3[CH:17]=[O:18])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[NH:38][N:37]=[N:36][N:35]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 178441929HCID 178441929, compound

Product 1

HCID 178441928HCID 178441928, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A mixture of the product of Example 5 (0.55 g), 4Å molecular sieves (powdered) (2.5 g), N-methylmorpholine-N-oxide (0.65 g) in a mixture of dry dichloromethane (10 ml) and dry acetonitrile (10 ml) was treated with tetrapropylammonium perruthenate (40 mg) at 0°. The mixture was stirred at 0° to ambient temperature for 1.5 h and filtered through "hyflo", and the solvent was evaporated. The residue was purified by flash column chromatography eluting with System F (400:400:10:10) to give a residue which was dissolved in a mixture of dichloromethane:ethyl acetate (2:1;25 ml) and washed with water (50 ml). (The pH of the aqueous solution was adjusted to 4 with aqueous sodium carbonate (2N)). The organic phase was, dried, filtered and evaporated to give the title compound as an off-white solid (0.31 g).

Workup

  1. filtrationfiltered through "hyflo"
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with System F (400:400:10:10)
  5. customto give a residue which
  6. washwashed with water (50 ml)
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-f5d15a15e9bb4a669358a1ecf4686727
Source dataset
uspto-grants-1993_10
Patent number
US05252593

Reaction notes

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