Sodium Hydroxide → HCID 76567981, compound

HRID 1728223Notes

Reaction equation

HRID 1728223 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[C:23]([O:25]C)=[O:24])[CH2:14][C:13](=[O:27])[NH:12][CH:11]3[C:28]([CH3:30])=[CH2:29])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[C:23]([OH:25])=[O:24])[CH2:14][C:13](=[O:27])[NH:12][CH:11]3[C:28]([CH3:30])=[CH2:29])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 76567988HCID 76567988, compound

Product 1

HCID 76567981HCID 76567981, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of racemic (2′R,3R,4′S)-6-chloro-4′-(5-chloro-2-methoxycarbonyl-phenyl)-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (60 mg, 0.13 mmol) in methanol (3.5 mL) was added a solution of NaOH (26 mg, 0.6 mmol) in water (1.5 mL). The mixture was heated at 70° C. for 3 h, concentrated 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 title compound as a white solid (33 mg). m/z (M+H)+: 445

Workup

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

Sources & evidence

ORD record
ord-31636d19037e48ae937a93730fa2b073
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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