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 1357418노트

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HRID 1357418 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-57d10500133c46a7997ee66e7a941aa1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589968B2

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