Hydrochloric Acid → HCID 69732411, compound

HRID 1072739Notes

Reaction equation

HRID 1072739 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]2[C:24]2[CH:43]=[CH:42][C:27]([O:28][C@H:29]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]([O:32]CC)=[O:31])=[CH:26][CH:25]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].Cl>C1COCC1.CO>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]2[C:24]2[CH:25]=[CH:26][C:27]([O:28][C@H:29]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]([OH:32])=[O:31])=[CH:42][CH:43]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86759777HCID 86759777, compound

Product 1

HCID 69732411HCID 69732411, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl (2R)-2-{4-[1-(4-decyloxyphenyl)-5-methyl-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate (870 mg, 1.49 mmol) in THF (30 ml) and methanol (15 ml) was added 1N aqueous potassium hydroxide solution(8 ml, 8 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. 760 mg (yield: 92.0%)

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-82969958eb974a0395b3472ea47262e9
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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