Tetrabutylammonium Fluoride → 5-Mercapto-indole-1-carboxylic acid tert-butyl ester

HRID 883951

Reaktionsgleichung

Reaktionsgleichung von HRID 883951
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17][Si](C(C)C)(C(C)C)C(C)C)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([SH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 670403485-Triisopropylsilanylsulfanyl-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 670402485-Mercapto-indole-1-carboxylic acid tert-butyl esterAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the product of Example 59B (203.7 mg, 0.502 mmol) in anhydrous tetrahydrofuran (4 mL) at −20° under a nitrogen atmosphere was treated with a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.552 mL, 0.552 mmol) and the reaction stirred at −20° for 15 minutes. The reaction was diluted with ethyl acetate (50 mL) and washed with water (2×25 mL) and brine (25 mL). The organic was dried over anhydrous magnesium sulfate, filtered, and concentrated by rotary evaporation under vacuum to provide a yellow oil. Purification by silica gel flash chromatography using 5% ethyl acetate/hexanes as eluent afforded the title compound (42 mg, 33%).

Aufarbeitung

  1. washwashed with water (2×25 mL) and brine (25 mL)
  2. dry with materialThe organic was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation under vacuum
  5. customto provide a yellow oil
  6. customPurification by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6648d0f1f86643ba8dd88c92f67c5063
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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