Hydrochloric Acid → (2R)-2-([4-[1-(4-Pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenyl]oxy)-3-phenylpropanoic acid

HRID 1072723Notes

Reaction equation

HRID 1072723 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:20]2[CH:25]=[CH:24][C:23]([O:26][C@H:27]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].Cl>C1COCC1.CO>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:20]2[CH:21]=[CH:22][C:23]([O:26][C@H:27]([CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86588894Ethyl (2R)-2-([4-[1-(4-pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenyl]oxy)-3-phenylpropanoate

Product 1

HCID 69732371(2R)-2-([4-[1-(4-Pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenyl]oxy)-3-phenylpropanoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl (2R)-2-([4-[1-(4-pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenyl]oxy)-3-phenylpropanoate (660 mg, 1.26 mmol) in THF (15 ml) and methanol (7 ml) was added 1N aqueous potassium hydroxide (4.0 ml, 4.0 mmol) and the mixture was stirred for 1 hour at room temperature. The reaction solution was neutralized with 1N 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. 615 mg, (yield 98%)

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-009d94c5fd2846ee8d4fd1282978fca7
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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