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 2181763Notes

Reaction equation

HRID 2181763 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e28fb4ca54504e8b93e1c3019909fe99
Source dataset
uspto-grants-2005_05
Patent number
US06893859B2

Reaction notes

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