Lithium Hydroxide → HCID 58127833, compound

HRID 1257415Notes

Reaction equation

HRID 1257415 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58127936HCID 58127936, compound

Product 1

HCID 58127833HCID 58127833, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (660 mg) obtained in Example 106a in tetrahydrofuran (5 ml) was added 2N lithium hydroxide aqueous solution (5 mL), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, and adjusted to pH 5-6 with 3N hydrochloric acid. The resulting precipitate was collected by filtration. The obtained solid was dissolved in tetrahydrofuran and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from ethanol to give the title compound (150 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. filtrationThe resulting precipitate was collected by filtration
  6. dissolutionThe obtained solid was dissolved in tetrahydrofuran
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8c0d83823e7b446f82d39d31889aff9d
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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