Sodium Hydroxide → HCID 76567942, compound

HRID 1095166Notes

Reaction equation

HRID 1095166 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH2:33][C:34]([C:37]([O:39]C)=[O:38])([CH3:36])[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.[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH2:33][C:34]([C:37]([OH:39])=[O:38])([CH3:36])[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 76567902HCID 76567902, compound

Product 1

HCID 76567942HCID 76567942, compoundYield 69.2%

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-(2-methoxycarbonyl-2-methyl-propoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (106 mg, 0.16 mmol) in methanol (6 mL) was added a solution of NaOH (30 mg, 0.75 mmol) in water (3 mL). The mixture was heated at 60° C. for 5 h, evaporated to remove methanol, cooled to room temperature, and acidified to “pH” 2 with HCl aq. The precipitate was collected and dried to give the title compound as a white solid (70 mg). m/z (M+H)+: 617

Workup

  1. customevaporated
  2. customto remove methanol
  3. temperaturecooled to room temperature
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-3de22f2ab1aa44c1b2e5bacaf9de65ee
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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