Acetic Acid → HCID 16223525, compound

HRID 390619Notes

Reaction equation

HRID 390619 reaction equation
[OH-].[Na+].[CH:3]1([NH:9][C:10](=[O:33])[N:11]([C:13]2[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22](/[CH:25]=[C:26](\[O:31][CH3:32])/[C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=3)[CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(O)(=O)C>O1CCCC1>[CH:3]1([NH:9][C:10](=[O:33])[N:11]([C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22](/[CH:25]=[C:26](\[O:31][CH3:32])/[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=3)[CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 16224426HCID 16224426, compound

Product 1

HCID 16223525HCID 16223525, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

2.2 mL (2.2 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 0.6 g (1.5 mmol) of methyl (Z)-3-[3′-(3-cyclohexyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylate in 12 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 4 hours. The reaction medium is acidified with 2.4 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. 500 mg (82%) of (Z)-3-[3′-(3-cyclohexyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the form of a white solid with a melting point of 192° 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-fcc1475b85c44feba5ce37eb103e0f20
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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