Sodium Hydroxide → HCID 76568082, compound

HRID 1728226Notes

Reaction equation

HRID 1728226 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]([C:36]([O:38]CC)=[O:37])([CH3:35])[CH3:34])=[C:6]([CH:8]2[C:13]3([C:21]4[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=4)[NH:15][C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1.[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]([C:36]([OH:38])=[O:37])([CH3:34])[CH3:35])=[C:6]([CH:8]2[C:13]3([C:21]4[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=4)[NH:15][C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 76567937HCID 76567937, compound

Product 1

HCID 76568082HCID 76568082, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of racemic (2′R,3R,4′S)-2′-[5-bromo-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (700 mg, 1.08 mmol) in methanol (20 mL) was added a solution of NaOH (120 mg, 3 mmol) in water (10 mL). The mixture was heated at 60° C. for 1.5 h, evaporated to remove most of methanol, cooled to room temperature, and acidified to “pH” 2 with aqueous HCl solution. The precipitate was collected and dried to give product as a white solid (610 mg). m/z (M+H)+: 617

Workup

  1. customevaporated
  2. customto remove most of methanol
  3. temperaturecooled to room temperature
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-38d5af24db8f4d2fbed15f1272d1605e
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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