Lithium Hydroxide → HCID 59509092, compound

HRID 1020083Notes

Reaction equation

HRID 1020083 reaction equation
C([O:3][C:4](=[O:26])[C:5]([NH:8][C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[N:15]=[CH:14][N:13]=1)=[O:10])([CH3:7])[CH3:6])C.[Li+].[OH-]>C1COCC1.O>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:9](=[O:10])[NH:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:26])=[O:3])[CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59509057HCID 59509057, compound

Product 1

HCID 59509092HCID 59509092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-2-methyl-propionic acid ethyl ester (LVI) (370 mg, 1.03 mmol) in a mixture of THF and water (1:1) was added a solution of LiOH (87.0 mg, 2.06 mmol) in water at ice bath temperature over 10 min and then allowed to stir for two hours at room temperature. THF was evaporated and the aqueous solution was acidified with 2N HCl. This aqueous phase was then extracted with ethyl acetate (2×100 ml), the combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor to afford 2-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-2-methyl-propionic acid as a white solid. Yield: 235 mg, 69.1%.

Workup

  1. customTHF was evaporated
  2. extractionThis aqueous phase was then extracted with ethyl acetate (2×100 ml)
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in a vacuum rotavapor

Sources & evidence

ORD record
ord-21d5f62dcdf64355a43b1ac73b782c2a
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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