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

HRID 1072725Notes

Reaction equation

HRID 1072725 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][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)[C:5]([C:23]2[CH:42]=[CH:41][C:26]([O:27][C@H:28]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]([O:31]CC)=[O:30])=[CH:25][CH:24]=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][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)[C:5]([C:23]2[CH:42]=[CH:41][C:26]([O:27][C@H:28]([CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]([OH:31])=[O:30])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86759772ethyl (2R)-2-{4-[5-methyl-1-(4-heptylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate

Product 1

HCID 69732570(2R)-2-{4-[5-methyl-1-(4-heptylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl (2R)-2-{4-[5-methyl-1-(4-heptylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate (1.03 g, 1.76 mmol) in THF (15 ml) and methanol (7 ml) was added 1N aqueous potassium hydroxide (5.3 ml, 5.3 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. 969 mg, (yield 99%)

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-a7b2a19c30394b2ab2829d89b3cd5b77
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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