Water → HCID 86632096, compound

HRID 504578Notes

Reaction equation

HRID 504578 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27]([O:29]C)=[O:28])([CH3:26])[CH3:25])[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27]([OH:29])=[O:28])([CH3:25])[CH3:26])[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86632097HCID 86632097, compound

Product 1

HCID 86632096HCID 86632096, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (600 mg, 1 mmol), NaOH (80 mg, 2 mmol), H2O (3 mL) and methanol (10 mL) was heated at 70° C. for 2 h. After cooled to room temperature, the solution was concentrated and then the residue was acidified to “pH” 2-3 by addition of concentrated HCl. The white solid was collected by filtration to give the title compound as a white solid (50 mg).

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe solution was concentrated
  3. additionby addition of concentrated HCl
  4. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-4ea29b84d22b44b983c4b78045c5794f
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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