Lithium hydroxide, monohydrate → HCID 66986854, compound

HRID 555348Notes

Reaction equation

HRID 555348 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:34])/[C:10](/[CH2:22][O:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.O.[OH-].[Li+]>O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:34])/[C:10](/[CH2:22][O:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66986742HCID 66986742, compound

Product 1

HCID 66986854HCID 66986854, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl (E)-4-(3-(1-methylpiperidin-4-ylamino)-2-((naphthalen-1-yloxy)methyl)-3-oxo-prop-1-enyl)benzoate (300 mg, 0.65 mM) obtained in Example (1-1-1) was dissolved in water (1 ml), and lithium hydroxide monohydrate (LiOH.H2O) (82 mg, 1.95 mM) was added thereto. The resulting mixture was stirred at room temperature for 10 mins, and further stirred at 50° C. for 3 hrs. After the completion of reaction, the reaction mixture was cooled to room temperature and ice water was poured thereinto, followed by removing the solvent under reduced pressure. Then, the resultant was cooled to 5, acidified with 2N hydrochloride solution to pH 4, extracted with chloroform/methanol (4/1) 3 times. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain 281 mg of the title compound (yield 97%).

Workup

  1. stirringfurther stirred at 50° C. for 3 hrs
  2. customAfter the completion of reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customby removing the solvent under reduced pressure
  5. temperatureThen, the resultant was cooled to 5
  6. extractionextracted with chloroform/methanol (4/1) 3 times
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d347a000f484115ab12dbbcef1a7472
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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