Ethoxalyl chloride → HCID 86605651, compound

HRID 1986478Notes

Reaction equation

HRID 1986478 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16]([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:15]2[C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].Cl[C:48](=[O:54])[C:49]([O:51][CH2:52][CH3:53])=[O:50]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([C:48](=[O:54])[C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16]([CH2:26][NH:27][C:28]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:34])=[C:15]2[C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 516892Sodium BicarbonateHCID 86605652HCID 86605652, compound

Product 1

HCID 86605651HCID 86605651, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.50 g, 0.89 mmol) in ethyl acetate (50 ml) was added saturated aqueous sodium hydrogen carbonate (50 ml), and the mixture was vigorously stirred at room temperature. Ethyl chloroglyoxylate (0.30 g, 2.2 mmol) was added dropwise to the obtained mixture and the mixture was vigorously stirred for 30 min. The organic layer was separated, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl {{2-[(tert-butoxycarbonyl)amino]ethyl}[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]amino}(oxo)acetate (0.53 g, yield 90%) as a white powder.

Workup

  1. stirringthe mixture was vigorously stirred for 30 min
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0233a2d2f15949648275f86ec234292d
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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