Sodium Chloride → HCID 59397860, compound

HRID 39751Notes

Reaction equation

HRID 39751 reaction equation
ClCCl.[OH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][C:14]2=[O:25])[CH:7]([C:26]([O:28][CH3:29])=[O:27])[CH2:6]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl-].[Na+]>C(Cl)(Cl)Cl.O>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17]([N:16]=[CH:15][C:14](=[O:25])[N:13]2[CH2:12][CH2:11][N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]2[C:26]([O:28][CH3:29])=[O:27])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 59398089HCID 59398089, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 59397860HCID 59397860, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 5 mL of a dichloromethane solution containing 0.2 g of methyl 4-hydroxy-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate, 0.3 g of molecular sieves 3A was added at room temperature under a nitrogen atmosphere, thereto was further added 0.18 g of pyridinium chlorochromate under cooling with ice, and the mixture was stirred at room temperature for 4 hours. Thereto was further added 90 mg of pyridinium chlorochromate over 1 hour and 40 minutes, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. The reaction mixture was added with water, chloroform and sodium chloride, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.10 g of a brown oily substance, methyl 1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)-4-oxopiperidine-2-carboxylate.

Workup

  1. additionwas added at room temperature under a nitrogen atmosphere
  2. temperatureunder cooling with ice
  3. customover 1 hour
  4. stirring40 minutes, and the mixture was stirred at the same temperature for 1 hour and 30 minutes
  5. customthe organic layer was separated
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9b26d35988f24623bbe139f593178688
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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