Dimethylformamide → HCID 68987739, compound

HRID 2249639Notes

Reaction equation

HRID 2249639 reaction equation
[CH2:1]([O:5][C:6]1[CH:27]=[C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:25]=[CH:24][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[C:14]([CH:18]=1)[C:15](O)=[O:16])=[O:9])[CH:2]([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH2:50])[CH3:46]>O1CCCC1.O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[CH:27]=[C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:25]=[CH:24][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[C:14]([CH:18]=1)[C:15]([NH:50][CH2:49][C:48]([O:47][CH2:45][CH3:46])=[O:51])=[O:16])=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 17816566HCID 17816566, compound

Product 1

HCID 68987739HCID 68987739, compoundYield 83.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

In 40 ml of tetrahydrofuran is dissolved 4.00 g of 5-(2,4-diisobutoxybenzoyl)-2-isobutoxybenzoic acid, to which are added 0.95 ml of oxalyl chloride and 20 μl of N,N-dimethylformamide. The mixture thus obtained is stirred at ambient temperature for one hour. To the reaction mixture are added 3.03 g of glycine ethyl ester hydrochloride and 4.2 ml of triethylamine successively, and the mixture thus obtained is stirred for one hour under reflux with heating. The reaction mixture is cooled to ambient temperature, chloroform and water are added, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1) to obtain 4.00 g of ethyl 2-{[5-(2,4-diisobutoxybenzoyl)-2-isobutoxybenzoyl]amino}acetate as a colorless oily product.

Workup

  1. customThe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred for one hour
  4. temperatureunder reflux
  5. temperaturewith heating
  6. temperatureThe reaction mixture is cooled to ambient temperature
  7. customthe organic layer is separated
  8. customThe organic layer thus obtained
  9. washis washed with water and saturated aqueous solution of sodium chloride successively
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent is distilled off under reduced pressure
  12. customThe residue thus obtained
  13. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b412c9130f3146498f64a5d5ee0a6a25
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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