Ethanol → HCID 59398334, compound

HRID 39792Notes

Reaction equation

HRID 39792 reaction equation
C(O)C.[O:4]=[C:5]1[CH:14]=[N:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[CH2:15][CH2:16][CH2:17][C:18]1([C:32]([O:34]CC)=[O:33])[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:19]1.[OH-].[Na+]>O>[O:4]=[C:5]1[CH:14]=[N:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[CH2:15][CH2:16][CH2:17][C:18]1([C:32]([OH:34])=[O:33])[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 59398042HCID 59398042, compound

Product 1

HCID 59398334HCID 59398334, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
57.5 °C

Procedure

To 2 mL of an ethanol solution containing 90 mg of ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate, 0.5 mL of 20% aqueous sodium hydroxide solution was added and stirred at 55-60° C. for 5 hours. 0.5 mL of 20% aqueous sodium hydroxide solution and 0.5 mL of water were added at the same temperature, and stirred at 55-60° C. for 1 hour. The mixture was cooled to the room temperature, and left to stand for 2 nights. The solvent was removed under reduced pressure, water was added, adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid, acetonitrile was added, and the solvent was removed under reduced pressure. Water was added, and the resulting solid was filtered to afford 35 mg of 4-(3-(2-oxoquinoxaline-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylic acid as a brown solid.

Workup

  1. additionwas added
  2. stirringstirred at 55-60° C. for 1 hour
  3. temperatureThe mixture was cooled to the room temperature
  4. waitleft
  5. waitto stand for 2 nights
  6. customThe solvent was removed under reduced pressure, water
  7. additionwas added
  8. additionwas added
  9. customthe solvent was removed under reduced pressure
  10. additionWater was added
  11. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-c8877660e778476d8db4c8cbf29f30e8
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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