Ethanol → HCID 59398334, compound

HRID 2193162Notes

Reaction equation

HRID 2193162 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-0feb5dcbeb334605847a8652b9cb1247
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…