HCID 13520514, compound → 3-[2-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indol-3-yl]propanoic acid

HRID 485317Notes

Reaction equation

HRID 485317 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH:23](C(OCC)=O)[C:24]([O:26]CC)=[O:25])=[CH:19][CH:18]=[CH:17][CH:16]=2>Cl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

3

Reactant 1

HCID 13520514HCID 13520514, compound

Product 1

HCID 135205153-[2-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indol-3-yl]propanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 22.8 g (0.05 mole) of [[2-(5-methyl-3-phenyl-4-isoxazolyl)-1H-indol-3-yl]methyl]propanedioic acid, diethyl ester and 150 ml of 12N hydrochloric acid is refluxed for 65 hours. The mixture is cooled and extracted with ether. The ether is washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated. The solid residue is then decolorized with charcoal and recrystallized from ether hexane to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-indole propionic acid m.p. 170° to 172° C.

Workup

  1. temperatureis refluxed for 65 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with ether
  4. washThe ether is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customrecrystallized from ether hexane

Sources & evidence

ORD record
ord-438bda3af5374adcac9996d908b9c729
Source dataset
uspto-grants-1985_08
Patent number
US04536499

Reaction notes

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