Sodium Hydroxide → HCID 54494969, compound

HRID 1585546Notes

Reaction equation

HRID 1585546 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][N:11]([CH2:24][C:25]([O:27]CC)=[O:26])[C:10](=[O:30])[CH2:9]1)=[O:7].[OH-].[Na+]>C(O)C>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][N:11]([CH2:24][C:25]([OH:27])=[O:26])[C:10](=[O:30])[CH2:9]1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86754412HCID 86754412, compound

Product 1

HCID 54494969HCID 54494969, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-1-(ethoxycarbonylmethyl)-5-(1H-indol-3-ylmethyl)piperazin-2-one (0.88 g) in ethanol (20 ml) was added 1N sodium hydroxide solution (1.58 ml). The mixture was stirred at the same temperature for 30 minutes and then at room temperature for 1 hour and 45 minutes. The mixture was concentrated under reduced pressure, and water and 1N hydrochloric acid (1.58 ml) were added to the residue under ice-cooling. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. After evaporation in vacuo, n-hexane was added to the crystalline residue and the resulting crystals were collected by filtration, washed with n-hexane, and dried to give (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-1-(carboxymethyl)-5-(1H-indol-3-ylmethyl)piperazin-2-one (0.76 g).

Workup

  1. waitat room temperature for 1 hour
  2. custom45 minutes
  3. concentrationThe mixture was concentrated under reduced pressure, and water and 1N hydrochloric acid (1.58 ml)
  4. additionwere added to the residue under ice-
  5. temperaturecooling
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customAfter evaporation in vacuo, n-hexane
  10. additionwas added to the crystalline residue
  11. filtrationthe resulting crystals were collected by filtration
  12. washwashed with n-hexane
  13. customdried

Sources & evidence

ORD record
ord-214913bafc324b9e8c0f1c4958ebbeeb
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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