Ethanol → HCID 22710590, compound

HRID 352815Notes

Reaction equation

HRID 352815 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[S:21][C:20]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:19]=3[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[C:27]([O:29]CC)=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[S:21][C:20]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:19]=3[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[C:27]([OH:29])=[O:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22711310HCID 22711310, compound

Product 1

HCID 22710590HCID 22710590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml) was dissolved 1-(tert-butoxycarbonyl)-4-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-2-(ethoxycarbonyl)piperazine (2.25 g), followed by the addition of ethanol (20 ml) and a 3N aqueous solution (3 ml) of sodium hydroxide. The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was adjusted to have pH of 1 to 2 by the addition of a 1N aqueous solution of hydrochloric acid. Ethyl acetate was then added and the organic layer was collected. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The solid thus precipitated was collected by filtration, whereby the title compound (2.17 g) was obtained as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionby the addition of a 1N aqueous solution of hydrochloric acid
  3. additionEthyl acetate was then added
  4. customthe organic layer was collected
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe solid thus precipitated
  9. filtrationwas collected by filtration, whereby the title compound (2.17 g)
  10. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-fdde599b7630406faff972cf97d4c77e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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