Triethylamine → HCID 69937937, compound

HRID 1058300Notes

Reaction equation

HRID 1058300 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH2:33]([C@@H:40]1[CH2:44][O:43][C:42](=[O:45])[NH:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Li]CCCC>C1COCC1>[CH2:33]([C@@H:40]1[CH2:44][O:43][C:42](=[O:45])[N:41]1[C:16](=[O:18])/[CH:15]=[CH:14]/[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 18672357HCID 18672357, compoundHCID 178418339Butyllithium

Product 1

HCID 69937937HCID 69937937, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of (2E)-3-[3-(tert-butoxycarbonyl)phenyl]prop-2-enoic acid from the previous step (0.186 g, 0.749 mmol) in THF (3 mL) was added triethylamine (0.110 mL, 0.787 mmol) and the mixture was cooled to −20° C. Pivaloyl chloride (0.0969 mL, 0.787 mmol) was added and then the reaction mixture was stirred at −20° C. for 15 min, warmed to 0° C. and stirred for 40 min. Meanwhile, to a cooled (−78° C.) solution of (R)-4-benzyl-2-oxazolidinone (0.305 g, 1.72 mmol) in THF (5 mL), was added nBuLi (1.1 mL, 1.6M in hexanes) dropwise and the mixture was stirred for 30 min. The slurry was warmed to 0° C. and added via cannula into the anion solution. After one hour, the reaction was quenched by the addition of 10 mL 20% aqueous NH4Cl solution, warmed to room temperature and extracted with 2×50 mL ether. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure, and chromatographed on a 4″ 25 mm SiO2 column using 18% EtOAc:hexanes. The clean fractions were combined and the solvent was removed under reduced pressure to give tert-butyl 3-{(1E)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxoprop-1-enyl}benzoate as an oil (0.273 g, 89%). TLC Rf=0.3 (1:4 EtOAc:hexanes, UV visualization); HPLC RT=2.9 min, method B; M+H=408.

Workup

  1. temperaturewarmed to 0° C.
  2. stirringstirred for 40 min
  3. stirringthe mixture was stirred for 30 min
  4. temperatureThe slurry was warmed to 0° C.
  5. additionadded via cannula into the anion solution
  6. waitAfter one hour
  7. customthe reaction was quenched by the addition of 10 mL 20% aqueous NH4Cl solution
  8. temperaturewarmed to room temperature
  9. extractionextracted with 2×50 mL ether
  10. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure
  14. customchromatographed on a 4″ 25 mm SiO2 column
  15. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-877d88254f824d588f1cee5c0d04359e
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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