Acetic Acid → HCID 19085527, compound

HRID 962762Notes

Reaction equation

HRID 962762 reaction equation
[C:1]1([CH:7]([O:24][C:25]2[CH:49]=[CH:48][C:28]([C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:40][CH2:41][CH2:42][C:43]([O:45]CC)=[O:44])[CH:32]=3)=[O:30])=[CH:27][CH:26]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C(O)(=O)C>C(O)C>[C:1]1([CH:7]([O:24][C:25]2[CH:49]=[CH:48][C:28]([C:29]([C:31]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:40][CH2:41][CH2:42][C:43]([OH:45])=[O:44])[CH:32]=3)=[O:30])=[CH:27][CH:26]=2)[CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 19085578HCID 19085578, compound

Product 1

HCID 19085527HCID 19085527, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-{3-{4-{1-phenyl-3-[4-(2-methoxyphenyl) piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate (1.89 g) obtained in Step 3 was dissolved in ethanol (20 ml). Potassium hydroxide (0.80 g) was added to the resultant solution and stirred for 3 hours at room temperature. After adding acetic acid (2 ml) to the reaction mixture, the solvent was distilled off. Water was added thereto, followed by extraction with ethyl acetate. The resultant extract was washed with brine and dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (methylene chloride: methanol=40:1), obtaining 1.68 g of 4-{3-{4-{1-phenyl-3-[4-(2-methoxyphenyl)piperazin-1-yl] propoxy}benzoyl}indol-1-yl}butanoic acid as amorphous powder.

Workup

  1. distillationthe solvent was distilled off
  2. additionWater was added
  3. extractionfollowed by extraction with ethyl acetate
  4. extractionThe resultant extract
  5. washwas washed with brine
  6. customdried
  7. distillationThe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (methylene chloride: methanol=40:1)

Sources & evidence

ORD record
ord-3cf95faebe0148258c589536d39f1082
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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