HCID 59926130, compound → HCID 18537529, compound

HRID 412210Notes

Reaction equation

HRID 412210 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:24]=[C:23]1[CH3:39])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8]CC)=[O:7])C>C1COCC1.[OH-].[Na+]>[CH3:39][C:23]1[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:4]([OH:40])=[O:3])[C:6]([OH:8])=[O:7])[C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:25]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:24]=1

Participants

4

Reactant 1

HCID 59926130HCID 59926130, compound

Product 1

HCID 18537529HCID 18537529, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

(Scheme 4 (S)) A solution of starting material 2-[5-(2-methyl-4,5-diphenyl-imidazol-1-yl)-pentyl]-2-phenyl-malonic acid diethyl ester (630 mg, 1.17 mmole) in THF (18 ml) and Sodium hydroxide (2N) (8 ml) was let stirred at 80° C. for 18 hrs. The next day, analysis by TLC indicated no significant change in the reaction. The THF solvent was removed by rotorvap. The residue was diluted in Methanol (20 ml). The reaction solution was let stirred under reflux for 2 hrs. Analysis by TLC indicated consumption of starting material. The organic solvent was removed by rotorvap. The residue was diluted with water (20 ml). The aqueous layer was extracted Diethyl Ether (2×20 ml). The organic layers were combined and extracted with Sodium Hydroxide (10%) (2×10 ml). The basic aqueous layers were combined and acidified with Hydrochloric acid (3N) to pH=1, then extracted with dichloromethane (2×20 ml). The organic layers were combined, dried over Sodium Sulfate and filtered. The resultant filtrate was concentrated in vacuo to provide product as a white solid (580 mg, quantitative yield). Mass Spec: 483.54 (MH+).

Workup

  1. customin the reaction
  2. customThe THF solvent was removed by rotorvap
  3. additionThe residue was diluted in Methanol (20 ml)
  4. temperatureunder reflux for 2 hrs
  5. customconsumption of starting material
  6. customThe organic solvent was removed by rotorvap
  7. additionThe residue was diluted with water (20 ml)
  8. extractionThe aqueous layer was extracted Diethyl Ether (2×20 ml)
  9. extractionextracted with Sodium Hydroxide (10%) (2×10 ml)
  10. extractionextracted with dichloromethane (2×20 ml)
  11. dry with materialdried over Sodium Sulfate
  12. filtrationfiltered
  13. concentrationThe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-660737c1714f4debb6434a2712146412
Source dataset
uspto-grants-2003_05
Patent number
US06562846B2

Reaction notes

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