Dimethylformamide → HCID 23077490, compound

HRID 1349457Notes

Reaction equation

HRID 1349457 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][O:11][C:10]=1[C:16]([OH:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([Cl:24])(=O)[C:20]([Cl:22])=O.C[N:26]([CH3:29])C=O>C(Cl)(Cl)Cl>[Cl:22][C:20]1[CH:1]=[C:2]([CH:3]=[CH:4][C:19]=1[Cl:24])[CH2:29][NH:26][C:16]([C:10]1[O:11][CH:12]=[CH:13][C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 217925463-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

Product 1

HCID 23077490HCID 23077490, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (0.4 g) prepared according to the method described in references (JP-A-2-502281 (WO88/06588), J. Med. Chem., 1999, 42, 4814–4823) in chloroform (30 ml) were added oxalyl chloride (0.21 ml) and dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solvent was evaporated under reduced pressure, toluene was added, the mixture was concentrated and dissolved in chloroform (5 ml). 3,4-Dichlorobenzylamine (0.23 ml) and triethylamine (0.34 ml) were added successively under ice-cooling, and the mixture was stirred under ice-cooling for 20 min. 5% Aqueous potassium hydrogen sulfate solution was added to the obtained reaction mixture and the mixture was extracted with. chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1–1:8) to give N-(3,4-dichlorobenzyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxamide (0.43 g).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure, toluene
  2. additionwas added
  3. concentrationthe mixture was concentrated
  4. dissolutiondissolved in chloroform (5 ml)
  5. addition3,4-Dichlorobenzylamine (0.23 ml) and triethylamine (0.34 ml) were added successively under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred under ice-
  8. temperaturecooling for 20 min
  9. addition5% Aqueous potassium hydrogen sulfate solution was added to the obtained reaction mixture
  10. extractionthe mixture was extracted with
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over sodium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1–1:8)

Sources & evidence

ORD record
ord-2ad07f7763fc42ddbab4648a593c52ec
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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