HCID 9855625, compound → HCID 69246152, compound

HRID 2371106Notes

Reaction equation

HRID 2371106 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[N:31]1([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:33][CH2:32]1>O1CCCC1.C(O)(C)(C)C.O>[CH2:37]([O:36][C:34]([NH:31][CH2:32][CH2:33][CH:10]([C:9](=[O:18])[CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:6][CH:5]=1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 3

HCID 9855625HCID 9855625, compoundHCID 23665647Potassium tert-butoxideHCID 58914664Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate

Product 1

HCID 69246152HCID 69246152, compoundYield 16.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound tert-butyl 5-biphenyl-4-yl-3-oxopentanoate (237 mg,) in tetrahydrofuran (4 ml) and tert-butyl alcohol (4 ml) at 0° C. under inert atmosphere was added potassium tert-butoxide (98 mg) and stirred for 20 minutes. To this at 0° C. was then added n-tetrabutylammonium iodide (27 mg) and benzyl aziridine-1-carboxylate (130 mg) and stirred the reaction mixture for 5 minutes. The resulting reaction mixture was warmed to room temperature and then further heated at 70° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue thus obtained was taken in water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography using 20% ethyl acetate in hexane as eluant to furnish the title compound (60 mg).

Workup

  1. customat 0° C.
  2. customThe resulting reaction mixture
  3. temperaturefurther heated at 70° C. for 2 hours
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue thus obtained
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layers were washed with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-210cc8daabfe4ceb80983698db88bd1f
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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