Sodium Hydroxide → HCID 76567925, compound

HRID 1728174Notes

Reaction equation

HRID 1728174 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:33])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][CH2:24][C:25]([O:27]C)=[O:26])[CH2:14][C:13](=[O:29])[NH:12][CH:11]3[C:30]([CH3:32])=[CH2:31])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:33])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][CH2:24][C:25]([OH:27])=[O:26])[CH2:14][C:13](=[O:29])[NH:12][CH:11]3[C:30]([CH3:32])=[CH2:31])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76567980HCID 76567980, compound

Product 1

HCID 76567925HCID 76567925, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Racemic (2′R,3R,4′S)-6-chloro-4′-(5-chloro-2-methoxycarbonylmethoxy-phenyl)-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (80 mg, 0.164 mmol) was dissolved in THF (10 mL). Then aqueous solution (1 mL) of NaOH (20 mg) was added. The mixture was refluxed for 1 h. After cooled to room temperature, the solution was concentrated and acidified to “pH” 2-3. The mixture was extracted with ethyl acetate. The organic layer was separated, dried and concentrated. The crude product (50 mg) was purified by Prep-HPLC to give the title compound as a white solid (14 mg).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. concentrationthe solution was concentrated
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product (50 mg) was purified by Prep-HPLC

Sources & evidence

ORD record
ord-7f6eba6c71004ea785dc39c92d30d752
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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