Lithium Hydroxide → HCID 59508958, compound

HRID 1020082Notes

Reaction equation

HRID 1020082 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[N:14]=[CH:13][N:12]=1)=[O:9])[CH3:6])C.[Li+].[OH-]>C1COCC1.O>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]1[N:14]=[CH:13][N:12]=[C:11]([NH:10][C:8](=[O:9])[NH:7][CH:5]([CH3:6])[C:4]([OH:25])=[O:3])[CH:16]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59508968HCID 59508968, compound

Product 1

HCID 59508958HCID 59508958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-propionic acid ethyl ester (LIV) (470 mg, 1.4 mmol) in a mixture of THF and water (1:1) was added a solution of LiOH (0.11 g, 2.7 mmol) in water at ice bath temperature over 30 min and then allowed to stir for 2 hours. THF was evaporated and the aq. solution was acidified with 2N HCl. This aq. phase was then extracted with ethyl acetate (2×100 ml), the separated and 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}-propionic acid (compound #32A) as a white solid. Yield: 223 mg, 50.4%.

Workup

  1. customTHF was evaporated
  2. extractionThis aq. phase was then extracted with ethyl acetate (2×100 ml)
  3. customthe separated
  4. washwere washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in a vacuum rotavapor

Sources & evidence

ORD record
ord-40030b8e69414ea98bd0b0f9a801d013
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

Loading…