Potassium Hydroxide → HCID 77580131, compound

HRID 1728181Notes

Reaction equation

HRID 1728181 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][CH:35]([C:37]([O:39]CC)=[O:38])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[Cl:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.[OH-].[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][CH:35]([C:37]([OH:39])=[O:38])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[Cl:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 77580095HCID 77580095, compound

Product 1

HCID 77580131HCID 77580131, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Racemic (2′R,3S,4′R)-4′-[5-bromo-2-(2-ethoxycarbonyl-2-methyl-ethoxy)-phenyl]-6-chloro-2′-(2,5-dichloro phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (150 mg, 0.22 mmol) was dissolved in THF (5 mL). Then aqueous solution (1 mL) of KOH (50 mg, 0.88 mmol) was added. The mixed solution was refluxed for 1 h. The mixture was cooled, concentrated and acidified to “pH” 2-3. The solution was concentrated and the residue was purified by Prep-HPLC to obtain a white solid (13 mg).

Workup

  1. temperatureThe mixed solution was refluxed for 1 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. concentrationThe solution was concentrated
  5. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-7e34031703124d7e84aebff432388e33
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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