Oxalyl chloride → HCID 44250625, compound

HRID 1964068Notes

Reaction equation

HRID 1964068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13]([OH:15])=O)=[C:4]([C:17]([O:19]C)=[O:18])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:27][C:28]1[O:32][CH:31]=[C:30]([C:33]2[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=2)[NH2:36])[CH:29]=1.C(=O)(O)[O-].[Na+]>C1COCC1.CC(N(C)C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13]([NH:36][C:35]2[CH:37]=[CH:38][CH:39]=[C:33]([C:30]3[CH:29]=[C:28]([CH3:27])[O:32][CH:31]=3)[CH:34]=2)=[O:15])=[C:4]([CH:3]=1)[C:17]([OH:19])=[O:18]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 510399542-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acidHCID 66876773HCID 66876773, compound

Product 1

HCID 44250625HCID 44250625, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

380 mg (2.2 mmol) of (2-[(4-chloro-2-(methoxycarbonyl)phenyl)amino]-2-oxoethoxy)acetic acid was dissolved in 7 mL of THF. 361 mg (2.9 mmol) of oxalyl chloride and a catalytic quantity of DMF were added thereto under ice-cooling, and stirred at room temperature for 2 hours. Thereafter, the solvent was distilled off under reduced pressure. The DMA solution of 380 mg (2.2 mmol) of 3-(5-methylfuran-3-yl)aniline was added to the resulting residue, and stirred for 1 hour. After completion of the reaction, an aqueous sodium bicarbonate solution (was added dropwise, and extraction was carried out using ethyl acetate. The organic layer was washed with an aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give 5-chloro-2-([(2-([3-(5-methylfuran-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 32%).

Workup

  1. temperatureunder ice-cooling
  2. distillationThereafter, the solvent was distilled off under reduced pressure
  3. stirringstirred for 1 hour
  4. customAfter completion of the reaction
  5. extractionextraction
  6. washThe organic layer was washed with an aqueous sodium bicarbonate solution and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customThe resulting crude product was separated
  11. custompurified

Sources & evidence

ORD record
ord-9506615d6f11454f99ed83c7b14e3752
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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