Sodium Hydroxide → (-)2-Ethoxy-3-[4-[2-[2-ethyl-6-oxo-4-phenyl-1,6-dihydropyrimidin-1-yl]ethoxy]phenyl]propanoic acid

HRID 840583Notes

Reaction equation

HRID 840583 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]=[C:21]2[CH2:33][CH3:34])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>O>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]=[C:21]2[CH2:33][CH3:34])=[CH:15][CH:16]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22137696(+/-) Ethyl 2-ethoxy-3-[4-[2-[2-ethyl-6-oxo-4-phenyl-1,6-dihydropyrimidin-1-yl]ethoxy]phenyl]propanoate

Product 1

HCID 22137687(-)2-Ethoxy-3-[4-[2-[2-ethyl-6-oxo-4-phenyl-1,6-dihydropyrimidin-1-yl]ethoxy]phenyl]propanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To the methanolic (15 mL) solution of (±) ethyl-2-ethoxy-3-[4-[2-ethyl-6-oxo-4-phenyl-1,6-dihydropyrimidin-1-yl]ethoxy]phenyl]propanoate (420 mg, 0.909 mmol) obtained in example 1 was added NaOH (365 mg, 9.125 mmol) in H2O (10 mL), the mixture was stirred at 25° C. for 1 hr, evaporated the solvent under reduced pressure. The residue was added to 50 mL of cold water and washed with ethyl acetate (2×50 mL). The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with water, brine, dried (Na2SO4) and evaporated the solvent, to give a stick compound, which was solidified by either long drying under vacuum or trituration with dry ether to give a white solid (380 mg, 96%) mp: 138-140° C.

Workup

  1. customevaporated the solvent under reduced pressure
  2. additionThe residue was added to 50 mL of cold water
  3. washwashed with ethyl acetate (2×50 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined ethyl acetate layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated the solvent
  8. customto give a stick compound, which
  9. dry with materialeither long drying under vacuum or trituration with dry ether

Sources & evidence

ORD record
ord-1b73f5477fe14e51bbdf6fa96c0cc662
Source dataset
uspto-grants-2002_04
Patent number
US06369067B1

Reaction notes

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