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

HRID 1072750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072750
[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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]([OH:30])=[O:29])=[CH:40][CH:41]=2)=[CH:42][CH:43]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86588899Ethyl (2R)-2-(4-{1-[3-(4-benzylphenoxy)propyl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate

Produkt 1

HCID 69730769(2R)-2-(4-{1-[3-(4-Benzylphenoxy)propyl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoic acidAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixed solution of ethyl (2R)-2-(4-{1-[3-(4-benzylphenoxy)propyl]-5-methyl-1H-pyrrol-2-yl}phenoxy)-3-phenylpropanoate (660 mg, 1.15 mmol) in THF (30 ml) and methanol (15 ml) was added 1N aqueous potassium hydroxide solution (6 ml, 6 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. 584 mg (yield: 92.8%)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9bf9e84f3f334b6bbd0d088bc8a94490
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911468B2

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