Acetic Acid → HCID 16226559, compound

HRID 390617Notes

Reaction equation

HRID 390617 reaction equation
[OH-].[Na+].[CH2:3]([NH:7][C:8](=[O:31])[N:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[O:29][CH3:30])/[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:10])[CH2:4][CH2:5][CH3:6].C(O)(=O)C>O1CCCC1>[CH2:3]([NH:7][C:8](=[O:31])[N:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[CH:19][C:20](/[CH:23]=[C:24](\[O:29][CH3:30])/[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:10])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 16224425HCID 16224425, compound

Product 1

HCID 16226559HCID 16226559, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

2.7 mL (2.7 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 0.7 g (1.8 mmol) of methyl (Z)-3-[3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylate in 12 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 2 hours. The reaction medium is acidified with 2.8 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 recrystallized from hot ethyl acetate. 530 mg (77%) of (Z)-3-[3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the form of a white solid with a melting point of 146° 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. customis recrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-2b08c7095c52424c8857a8f1cb733973
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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