Lithium hydroxide, monohydrate → HCID 70046769, compound

HRID 1378987Notes

Reaction equation

HRID 1378987 reaction equation
C[O:2][C:3]([C:5]1[CH:30]=[CH:29][C:8](/[CH:9]=[CH:10]\[C:11]2[N:19]([CH3:20])[C:18]3[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH3:24])[C:15](=[O:25])[N:14]([CH2:26][CH2:27][CH3:28])[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:20][N:19]1[C:18]2[C:17](=[O:21])[N:16]([CH2:22][CH2:23][CH3:24])[C:15](=[O:25])[N:14]([CH2:26][CH2:27][CH3:28])[C:13]=2[N:12]=[C:11]1/[CH:10]=[CH:9]\[C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70046713HCID 70046713, compound

Product 1

HCID 70046769HCID 70046769, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 8 (2.64 g, 6.44 mmol) obtained in Example 7 was dissolved in a solvent mixture of 60 ml of dioxane and 40 ml of water. To the solution was added 1.08 g (25.8 mmol) of lithium hydroxide monohydrate, and the resulting mixture was stirred at room temperature for one hour. After neutralization with 1N HCl, the mixture was extracted three times with ethyl acetate. The combined extract was dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The resulting crude crystals were recrystallized from toluene/cyclohexane to give 2.26 g (yield 89%) of Compound 18 as a yellow powder.

Workup

  1. extractionAfter neutralization with 1N HCl, the mixture was extracted three times with ethyl acetate
  2. extractionThe combined extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customfollowed by evaporation under reduced pressure
  5. customThe resulting crude crystals were recrystallized from toluene/cyclohexane

Sources & evidence

ORD record
ord-c7ec8892e1ac45b2b0fff779740c645c
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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