Ethyl isocyanate → (11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate

HRID 14374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14374
[C:1]([O:4][CH2:5][C:6](=[O:35])[C@:7]1([OH:34])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:31])([C@@H:22]([O:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:32])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][C@@H:8]1[CH3:33])(=[O:3])[CH3:2].[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37].COC(C)(C)C.CCCCCC.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:36]([NH:38][C:39](=[O:40])[O:34][C@:7]1([C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:31])([C@@H:22]([O:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:32])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][C@@H:8]1[CH3:33])[C:6](=[O:35])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH3:37]

Komponenten

5

Edukt 3

HCID 8022Ethyl isocyanateHCID 11352672(11beta,16beta)-9-Fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-[(trimethyl-silyl)oxy]-pregna-1,4-dien-21-yl acetateHCID 131728161t-Butyl methyl ether hexane chloroform

Produkt 1

HCID 68717367(11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamateAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of (11β,16β)-9-fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-[(trimethyl-silyl)oxy]-pregna-1,4-dien-21-yl acetate (3.11 g, 6.15 mmol) in 41 mL of toluene was added neat ethyl isocyanate (20.5 mL, 259 mmol) and the mixture was refluxed for 48 hours. The resulting solution was cooled to room temperature and evaporated under vacuum to leave a slightly gummy solid. Flash chromatography through a 1 kg column of silica gel eluting with t-butyl methyl ether/hexane/chloroform (1:1:1) gave 2.22 g of the title compound as a white solid.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 48 hours
  2. customevaporated under vacuum
  3. customto leave a slightly gummy solid

Quellen und Nachweise

ORD-Eintrag
ord-a6663e1989114dada27ab5d109dc064c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732432B2

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