tert-Butanol → tert-butyl (2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoate

HRID 2296863ノート

反応式

HRID 2296863 の反応式
[O:1]=[C:2]([C@H:20]([CH3:36])[C@@H:21]([O:27][C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29])[C@@H:22]([CH3:26])[CH2:23][CH:24]=[CH2:25])[C:3]([CH3:19])([CH3:18])[C@@H:4]([O:10][Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13])[C@H:5]([CH3:9])[C:6]([OH:8])=[O:7].[C:37](O)([CH3:40])([CH3:39])[CH3:38].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:1]=[C:2]([C@H:20]([CH3:36])[C@@H:21]([O:27][C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:33])[Cl:34])=[O:29])[C@@H:22]([CH3:26])[CH2:23][CH:24]=[CH2:25])[C:3]([CH3:19])([CH3:18])[C@@H:4]([O:10][Si:11]([CH2:12][CH3:13])([CH2:16][CH3:17])[CH2:14][CH3:15])[C@H:5]([CH3:9])[C:6]([O:8][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:7]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 86586617(2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoic acid

生成物 1

HCID 86586618tert-butyl (2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoic acid (11.8 g), tert-butanol (4.5 g), and 4-dimethylaminopyridine (0.2 g) in 20 mL of CH2Cl2 is cooled on ice and treated with dicyclohexylcarbodiimide (4.6 g) over a 5-minute period. The mixture is allowed to warm to ambient temperature and is stirred for 3 hours. The slurry is diluted with CH2Cl2 and filtered, and the filtrate is washed sequentially with sat. aq. citric acid, 5% NaHCO3, and brine. The solution is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

後処理

  1. filtrationfiltered
  2. washthe filtrate is washed sequentially with sat. aq. citric acid, 5% NaHCO3, and brine
  3. dry with materialThe solution is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product is purified by chromatography on SiO2

出典と根拠

ORDレコード
ord-34bdff1f397143d69d49387d198c4afd
出典データセット
uspto-grants-2002_12
特許番号
US06489314B1

反応ノート

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