Sodium Hydroxide → HCID 11734695, compound

HRID 1741849Notes

Reaction equation

HRID 1741849 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:22][C:23]2[CH:24]=[C:25]([CH:45]=[CH:46][CH:47]=2)[C:26]([C:28]2[CH:29]=[C:30]([CH2:37][CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])[N:31]3[C:36]=2[CH:35]=[CH:34][CH:33]=[CH:32]3)=[O:27])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>C(O)C>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:11]([NH:22][C:23]2[CH:24]=[C:25]([CH:45]=[CH:46][CH:47]=2)[C:26]([C:28]2[CH:29]=[C:30]([CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[N:31]3[C:36]=2[CH:35]=[CH:34][CH:33]=[CH:32]3)=[O:27])[C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=2)=[CH:17][CH:16]=1)[CH:19]([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11072251Ethyl 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]butyrate

Product 1

HCID 11734695HCID 11734695, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]-butyrate (279 mg) in ethanol (10 ml) was added 4N sodium hydroxide (0.44 ml). Stirring was continued for 1 hour at 40° C. The reaction mixture was evaporated in vacuo, then added a solution of potassium dihydrogen phosphate (300 mg) in water and 1N hydrochloric acid (26 ml), and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel eluting with ethyl acetate to give 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]butyric acid (229 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionadded a solution of potassium dihydrogen phosphate (300 mg) in water and 1N hydrochloric acid (26 ml)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-7f0f3c348cd740c1a6e3db3c78351091
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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