Water → HCID 12043734, compound

HRID 842957Notes

Reaction equation

HRID 842957 reaction equation
[C:1]([C:3]1([C:15]2[C:24]3[O:23][CH2:22][CH2:21][O:20][C:19]=3[C:18]([O:25][CH3:26])=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([O:12]CC)=[O:11])[CH2:5][CH2:4]1)#[N:2].[OH-].[Na+].O.C(OCC)(=O)C>C(O)C>[C:1]([C:3]1([C:15]2[C:24]3[O:23][CH2:22][CH2:21][O:20][C:19]=3[C:18]([O:25][CH3:26])=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([OH:12])=[O:11])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12043733HCID 12043733, compound

Product 1

HCID 12043734HCID 12043734, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound 20 (0.41 g, 1.1 mmol) obtained in Example 19 in ethanol (4.1 mL) was added a 2 mol/L aqueous solution of sodium hydroxide (1.1 mL), and the mixture was stirred at room temperature for 1 hour and then stirred at 60° C. for 20 minutes. The mixture was allowed to cool, and water and ethyl acetate were added to the mixture, followed by separating into an organic layer and an aqueous layer. The aqueous layer was acidified with 6 mol/L aqueous hydrochloric acid and extracted with ethyl acetate, and the extract was washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo, toluene was added to the residue, and the mixture was evaporated in vacuo. To the residue was added diisopropyl ether, and the precipitated solid was collected by filtration and recrystallized from ethanol to give Compound 21 (0.13 g, 36%) as a mixture of isomers in white crystals.

Workup

  1. stirringstirred at 60° C. for 20 minutes
  2. temperatureto cool
  3. customby separating into an organic layer
  4. extractionextracted with ethyl acetate
  5. washthe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated in vacuo, toluene
  8. additionwas added to the residue
  9. customthe mixture was evaporated in vacuo
  10. additionTo the residue was added diisopropyl ether
  11. filtrationthe precipitated solid was collected by filtration
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dc1b89fc36ac4afb84689fb8c0c3eaa3
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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