Triethylamine → HCID 68882697, compound

HRID 2111015Notes

Reaction equation

HRID 2111015 reaction equation
[Si]([O:8][CH:9]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1)[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(C(C)(C)C)(C)C.[SH:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(Cl)(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[OH:8][CH:9]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][S:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:22][CH:23]=1)[CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 18050Methyl 3-mercaptopropionateHCID 11078149TBAF tetrahydrofuranHCID 68881769HCID 68881769, compound

Product 1

HCID 68882697HCID 68882697, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (40 ml) of tert-butyl 3-(tert-butyldimethylsilyl)oxy-3-(4-chloromethylphenyl)propionate (3.25 g, 8.44 mmol) in chloroform were added methyl 3-mercaptopropionate (1.12 g, 9.32 mmol), triethylamine (2.4 ml, 17.29 mmol), and tetrabutylammonium iodide (156 mg, 0.42 mmol), and the mixture was stirred overnight at 50° C. The solvent was evaporated under reduced pressure and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure again. The obtained crude product was dissolved in THF (35 ml), 1M tetrabutylammonium fluoride-THF solution (8.5 ml, 8.50 mmol) was added, and the mixture was stirred at room temperature for 4 hours. The solvent was evaporated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the title compound (711 mg, 24%).

Workup

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure again
  7. customThe obtained crude product
  8. stirringthe mixture was stirred at room temperature for 4 hours
  9. customThe solvent was evaporated under reduced pressure, water
  10. additionwas added
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customthe obtained crude product
  16. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-70ae2a5b52424d439b33263e9acd4974
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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