Hydrochloric Acid → HCID 22400516, compound

HRID 260841Notes

Reaction equation

HRID 260841 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:37][CH2:38][CH3:39])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH:21]=2)=[O:19])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].Cl>C(O)C.O1CCOCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:37][CH2:38][CH3:39])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:21]=2)=[O:19])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22400460Ethyl 4-[3-[8-(4-isobutylphenyl)undecanoyl]1-indolyl]butyrate

Product 1

HCID 22400516HCID 22400516, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 4-[3-[8-(4-isobutylphenyl)undecanoyl]1-indolyl]butyrate obtained in Ex. 15 (44 mg) and 1N solution of sodium hydroxide (0.5 ml) in ethanol (1 ml) and 1,4-dioxane (2 ml) was stirred at room temperature for 3 hours. The mixture was then acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic solution was washed with water and brine, and dried over magnesium sulfate. Evaporation of the solvent afforded 4-[3-[8-(4-isobutylphenyl)-undecanoyl]1-indolyl]butyric acid as an oil (41 mg).

Workup

  1. customobtained in Ex
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-56feb2a7ef3b4b6eb050ffea480476b6
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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