Water → HCID 46193614, compound

HRID 555645Notes

Reaction equation

HRID 555645 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[C:11]3[Se:23][CH:22]=[CH:21][C:12]=3[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1)=[O:4].C(OCC)(=O)C.O>[OH-].[Na+]>[OH:4][C:3]([C:5]1[O:9][C:8]([C:10]2[C:11]3[Se:23][CH:22]=[CH:21][C:12]=3[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 46193499HCID 46193499, compound

Product 1

HCID 46193614HCID 46193614, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Compound 34 (1.49 g, 0.004 mole) in 40 ml of 10% NaOH solution was heated under refluxing for 2 h. The progress of the hydrolysis reaction was monitored by TLC with ethyl acetate (EA). When the reaction was completed, the reaction mixture was poured into water to stop the reaction, and then was extracted with toluene. The aqueous layer was recovered, and acidified with 10% HCl solution, which was then extracted with EA. The organic layer was recovered and dried over MgSO4 and filtered. The solvent of the filtrate was evaporated under a reduced pressure, and the residue was then recrystallized from EA to afford compound 48 in brown columnar crystals (0.76 g). Yield: 78%; mp 234-237° C.

Workup

  1. temperatureunder refluxing for 2 h
  2. customThe progress of the hydrolysis reaction
  3. customthe reaction
  4. extractionwas extracted with toluene
  5. customThe aqueous layer was recovered
  6. extractionwas then extracted with EA
  7. customThe organic layer was recovered
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent of the filtrate was evaporated under a reduced pressure
  11. customthe residue was then recrystallized from EA

Sources & evidence

ORD record
ord-11647bcce76843e6b79805b033ba00f4
Source dataset
uspto-grants-2011_11
Patent number
US08053459B1

Reaction notes

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