Trichloroacetyl chloride → HCID 54431643, compound

HRID 257580Notes

Reaction equation

HRID 257580 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[C:8](=[N:12][O:13][CH3:14])[C:9]([NH2:11])=O)=[C:4]([F:23])[CH:3]=1.ClC(Cl)(Cl)C(Cl)=O>C(N(CC)CC)C>[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[C:8](=[N:12][O:13][CH3:14])[C:9]#[N:11])=[C:4]([F:23])[CH:3]=1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 54465975HCID 54465975, compound2×

Product 1

HCID 54431643HCID 54431643, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by reaction of 3-(4-bromo-2-fluorobenzyl)-2-methoxyimino-4-oxooctanamide (from Step H) with trichloroacetyl chloride in the presence of triethylamine according to the procedure of Example 4, Step F. Alternatively, the following procedure is used. To 1 mmol of the amide from Step H is added about 12 mL of polyphosphate ester (PPE) [M. Cava, M. Lakshmikantham, and M. Mitchell, J. Org. Chem., 34, 2665 (1969)] solution, consisting of approximately a 2:1 ratio of PPE and CDCl3 (used as a surrogate for alcohol-free chloroform). The mixture is stirred at reflux under N2 for about 3 hours, and then the solvent is removed by concentration in vacuo. The residue is cooled in an ice bath and treated with an excess of saturated aqueous Na2CO3. The mixture is stirred for 1 hour and then extracted with ethyl acetate. The organic phase is washed further with H2O, then dried over Na2SO4, filtered, and concentrated. The residue is purified by column chromatography on silica gel (elution with hexane-EtOAc) to afford the title compound.

Workup

  1. temperatureat reflux under N2 for about 3 hours
  2. customthe solvent is removed by concentration in vacuo
  3. temperatureThe residue is cooled in an ice bath
  4. additiontreated with an excess of saturated aqueous Na2CO3
  5. stirringThe mixture is stirred for 1 hour
  6. extractionextracted with ethyl acetate
  7. washThe organic phase is washed further with H2O
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue is purified by column chromatography on silica gel (elution with hexane-EtOAc)

Sources & evidence

ORD record
ord-9dc9319f183a44f99c580020c9698ed6
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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