Hydrochloric Acid → (2R)-2-{4-[5-Methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoic acid

HRID 1072728Notes

Reaction equation

HRID 1072728 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]2[CH:40]=[CH:39][C:24]([O:25][C@H:26]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>C1COCC1.CO>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]2[CH:22]=[CH:23][C:24]([O:25][C@H:26]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]([OH:29])=[O:28])=[CH:39][CH:40]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86759769Ethyl (2R)-2-{4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate

Product 1

HCID 69731807(2R)-2-{4-[5-Methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl (2R)-2-{4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate (1.12 g, 2.20 mmol) in THF (20 ml) and methanol (10 ml) was added 1N aqueous potassium hydroxide (6.6 ml, 6.6 mmol) and the mixture was stirred for 1 hour at room temperature. The reaction solution was neutralized with 1N aqueous hydrochloric acid, extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to give the object compound as an oily substance. 1.00 g, (yield 94%)

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-03f505ea70c84a6a9beaf0507f29a815
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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