Acetic Acid → HCID 16223528, compound

HRID 390621Notes

Reaction equation

HRID 390621 reaction equation
[OH-].[Na+].[CH3:3][O:4]/[C:5](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:33])[C:24]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:25])[CH:18]=2)=[CH:13][CH:12]=1)/[C:6]([O:8]C)=[O:7].C(O)(=O)C>O1CCCC1>[CH3:3][O:4]/[C:5](=[CH:10]\[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:33])[C:24]([NH:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:25])[CH:18]=2)=[CH:15][CH:16]=1)/[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 16223527HCID 16223527, compound

Product 1

HCID 16223528HCID 16223528, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

2.5 mL (2.5 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 0.7 g (1.7 mmol) of methyl (Z)-2-methoxy-3-[3′-(1-methyl-3-phenylureido)biphenyl-4-yl]acrylate in 12 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 4 hours. The reaction medium is acidified with 2.6 mL of 1 N acetic acid solution and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is filtered from hot ethanol. 410 mg (60%) of (Z)-2-methoxy-3-[3′-(1-methyl-3-phenylureido)biphenyl-4-yl]acrylic acid are obtained in the form of a white solid with a melting point of 223° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. filtrationis filtered from hot ethanol

Sources & evidence

ORD record
ord-70862dec43294a92825039ab0d2ebf1e
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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