Hydrogen Peroxide → (2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoic acid

HRID 348256Notes

Reaction equation

HRID 348256 reaction equation
[O:1]=[C:2]([C@H:32]([CH3:48])[C@@H:33]([O:39][C:40]([O:42][CH2:43][C:44]([Cl:47])([Cl:46])[Cl:45])=[O:41])[C@@H:34]([CH3:38])[CH2:35][CH:36]=[CH2:37])[C:3]([CH3:31])([CH3:30])[C@@H:4]([O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[C@H:5]([CH3:21])[C:6](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:7].OO.[OH-].[Li+].S([O-])([O-])=[O:54].[Na+].[Na+]>C1COCC1.O.O>[O:1]=[C:2]([C@H:32]([CH3:48])[C@@H:33]([O:39][C:40]([O:42][CH2:43][C:44]([Cl:47])([Cl:46])[Cl:45])=[O:41])[C@@H:34]([CH3:38])[CH2:35][CH:36]=[CH2:37])[C:3]([CH3:30])([CH3:31])[C@@H:4]([O:22][Si:23]([CH2:28][CH3:29])([CH2:24][CH3:25])[CH2:26][CH3:27])[C@H:5]([CH3:21])[C:6]([OH:7])=[O:54]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 69507500HCID 69507500, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of (4S)-3-[(2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoyl]-4-benzyloxazolidinone (21.5 g) in 125 mL of 4:1 THF/water is cooled on ice and treated with 10.2 mL of 30% H2O2 followed by a solution of lithium hydroxide (0.96 g) in 50 mL of water. After 1 hour, a solution of sodium sulfite (12.6 g) in 75 mL of water is added, and the mixture is adjusted to pH 3 and concentrated under vacuum. The resulting slurry is extracted with ethyl acetate. The extract is washed with brine, dried over MgSO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionThe resulting slurry is extracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product is purified by chromatography on SiO2

Sources & evidence

ORD record
ord-032f8c5c70834d59beb956241e8e953a
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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