Lithium Hydroxide → HCID 59509102, compound

HRID 1020063Notes

Reaction equation

HRID 1020063 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:26])[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:4].[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:10]([N:6]2[CH2:7][CH2:8][CH2:9][CH:5]2[C:3]([OH:4])=[O:2])=[O:26])[CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59509124HCID 59509124, compound

Product 1

HCID 59509102HCID 59509102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester (LX) (500 mg, 1.40 mmol) in a mixture of THF and water (1:1) was added a solution of LiOH (0.118 g, 2.80 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 1-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-pyrrolidine-2-carboxylic acid as a white solid. Yield: 210 mg, 43.8%.

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-a3fd876da137489896eb87c2447030cb
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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