Lithium Hydroxide → HCID 178497118, compound

HRID 2270978Notes

Reaction equation

HRID 2270978 reaction equation
C[O:2][C:3](=[O:29])[C:4]([OH:28])=[CH:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][O:19][CH3:20])[CH:15]=2)[N:10]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:9]=1)=[O:7].[OH-].[Li+]>O1CCOCC1>[C:24]([O:23][C:21]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][CH:12]=2)[C:8]([C:6](=[O:7])[CH:5]=[C:4]([OH:28])[C:3]([OH:29])=[O:2])=[CH:9]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178497117HCID 178497117, compound

Product 1

HCID 178497118HCID 178497118, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.345 g (0.85 mmol) of the ester derivative obtained in above (1) in dioxane (7 ml) was added 1.7 ml of 1 N lithium hydroxide. The mixture was stirred for 1.5 hours at room temperature. The Solvent was removed under reduced pressure at room temperature and the residue was dissolved in water. The aqueous layer was washed twice with ethyl acetate and neutralized with 1 N hydrochloric acid (1.7 ml) and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried. The solvent was removed and the obtained crystal was washed with ethyl acetate to give 0.28 g of the titled compound.

Workup

  1. customThe Solvent was removed under reduced pressure at room temperature
  2. dissolutionthe residue was dissolved in water
  3. washThe aqueous layer was washed twice with ethyl acetate and neutralized with 1 N hydrochloric acid (1.7 ml)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. customdried
  7. customThe solvent was removed
  8. washthe obtained crystal was washed with ethyl acetate

Sources & evidence

ORD record
ord-2e358cc77c874a51b7a733a19c0345a4
Source dataset
uspto-grants-2001_12
Patent number
US06333323B1

Reaction notes

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