HCID 68929525, compound → HCID 57704583, compound

HRID 2406051Notes

Reaction equation

HRID 2406051 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:20]([CH2:32][O:33][Si](C(C)(C)C)(C)C)[CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:20]([CH2:32][OH:33])[CH:19]=2)[CH2:9][O:10][C:11]([CH3:15])([CH3:14])[O:12][CH2:13]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68929525HCID 68929525, compound

Product 1

HCID 57704583HCID 57704583, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Compound 34-4 (11.7 g) was dissolved in 1,4-dioxane (150 ml), 10% palladium carbon (12.0 g) was added, and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere. The inside of the reaction container was displaced with nitrogen, the solution was filtrated, and the filtrate was concentrated. To a solution of the obtained residue in tetrahydrofuran (100 ml) was added 1M tetrabutylammonium fluoride-tetrahydrofuran solution (20 ml) under ice-cooling, and the mixture was stirred for 1.5 hr under ice-cooling. A solution of 1M tetrabutylammonium fluoride-tetrahydrofuran solution (10 ml) was added, and the mixture was further stirred for 4 hr under ice-cooling. Water was added to the reaction mixture, the mixture extracted with ethyl acetate, washed successively with water saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object product (5.99 g) as a pale-brown oil.

Workup

  1. filtrationthe solution was filtrated
  2. concentrationthe filtrate was concentrated
  3. additionTo a solution of the obtained residue in tetrahydrofuran (100 ml) was added 1M tetrabutylammonium fluoride-tetrahydrofuran solution (20 ml) under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred for 1.5 hr under ice-
  6. temperaturecooling
  7. additionA solution of 1M tetrabutylammonium fluoride-tetrahydrofuran solution (10 ml) was added
  8. stirringthe mixture was further stirred for 4 hr under ice-
  9. temperaturecooling
  10. additionWater was added to the reaction mixture
  11. extractionthe mixture extracted with ethyl acetate
  12. washwashed successively with water saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69ee08634ea64286bff46048cdeea93e
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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