Sodium Hydroxide → HCID 76568043, compound

HRID 1728158Notes

Reaction equation

HRID 1728158 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:38])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([C:30]#[C:31][Si](C)(C)C)[CH:27]=[CH:26][C:25]=3[O:36][CH3:37])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:38])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([C:30]#[CH:31])[CH:27]=[CH:26][C:25]=3[O:36][CH3:37])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76568155HCID 76568155, compound

Product 1

HCID 76568043HCID 76568043, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-methoxy-5-(2-trimethylsilanyl-ethynyl)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′-dione (50 mg, 0.088 mmol) in MeOH (2 ml) was added 2N NaOH dropwise. The reaction was stirred for 30 min and extracted with EtOAc. The combined organic extract was dried and concentrated and was purified by flash chromatography, eluting with CH2Cl2, then EtOAc. Recrystallization gave the title compound as a white solid (13 mg, 13% yield). MS (H+), 491

Workup

  1. extractionextracted with EtOAc
  2. extractionThe combined organic extract
  3. customwas dried
  4. concentrationconcentrated
  5. customwas purified by flash chromatography
  6. washeluting with CH2Cl2
  7. customRecrystallization

Sources & evidence

ORD record
ord-78e1eb4a261642dc9816c45552e93a9e
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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