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

HRID 14374ノート

反応式

HRID 14374 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 68717367(11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate収率 62.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a6663e1989114dada27ab5d109dc064c
出典データセット
uspto-grants-2010_06
特許番号
US07732432B2

反応ノート

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