Lithium Hydroxide → [3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944494
C[O:2][C:3](=[O:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[S:20][N:19]=[C:18]([Cl:21])[C:17]=2[S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[C:6]1[CH3:31].[OH-].[Li+]>O1CCCC1>[C:25]1([S:22]([C:17]2[C:18]([Cl:21])=[N:19][S:20][C:16]=2[CH2:15][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=3)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]=2[CH3:31])(=[O:23])=[O:24])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67044606[3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Produkt 1

HCID 58201238[3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acidAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of [3-(4-benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.065 g), tetrahydrofuran (20 mL) and 1.0 M aqueous lithium hydroxide solution (4.0 mL) was stirred at room temperature for 5 minutes. The mixture was concentrated under reduced pressure, acidified by the addition of 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 19:1 by volume) to afford the title compound as a white solid (0.050 g).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionacidified by the addition of 1.0 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (1:19 to 19:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-2e8f79801d6b44f28ebc81a7dc621ae8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394836B2

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