Hydrochloric Acid → HCID 69731019, compound

HRID 1072757Notes

Reaction equation

HRID 1072757 reaction equation
[CH2:1]([C:8]1[CH:43]=[CH:42][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[C:22]2[CH:41]=[CH:40][C:25]([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:24][CH:23]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[K+].Cl>C1COCC1.CO>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[C:22]2[CH:23]=[CH:24][C:25]([O:26][C@H:27]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]([OH:30])=[O:29])=[CH:40][CH:41]=2)=[CH:42][CH:43]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86759782HCID 86759782, compound

Product 1

HCID 69731019HCID 69731019, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl (2R)-2-(4-{l-[3-(4-heptylphenoxy)propyl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate (480 mg, 0.825 mmol) in THF (15 ml) and methanol (15 ml) was added 1N aqueous potassium hydroxide solution (3 ml, 3 mmol) and the mixture was stirred for 1 hour at room temperature. The reaction solution was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the object compound as an oily substance. 353 mg (yield: 77.3%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  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 (hexane:ethyl acetate=1:1)
  6. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-32442daaa88941a28abb9110420055c4
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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