Water → HCID 86632094, compound

HRID 504574Notes

Reaction equation

HRID 504574 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[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]([CH3:38])[CH:35]=[CH:34][C:33]=3[O:39][CH3:40])[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:41])[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]([CH3:38])[CH:35]=[CH:34][C:33]=3[O:39][CH3:40])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86632093HCID 86632093, compound

Product 1

HCID 86632094HCID 86632094, compoundYield 21.6%

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-methyl-2-methoxy-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (100 mg, 0.167 mmol), NaOH (33.5 mg, 0.837 mmol), H2O (2 mL) and methanol (3 mL) was heated at 70° C. for 1 h. Then methanol was removed by vacuum and the aqueous solution was acidified to “pH” 1-2 by addition of concentrated HCl aqueous solution. The precipitate was collected by filtration and washed with CH2Cl2 twice to give the title compound as a white solid (21 mg).

Workup

  1. customThen methanol was removed by vacuum
  2. additionby addition of concentrated HCl aqueous solution
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with CH2Cl2 twice

Sources & evidence

ORD record
ord-7a478a9ea19246c69451addef349d815
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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