Acetic Acid → HCID 16226560, compound

HRID 390618Notes

Reaction equation

HRID 390618 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]([CH3:32])[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[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]([CH3:32])[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[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 57543178HCID 57543178, compound

Product 1

HCID 16226560HCID 16226560, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

2.9 mL (2.9 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 0.8 g (1.9 mmol) of methyl (Z)-2-methoxy-3-[3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate in 15 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 4 hours. The reaction medium is acidified with 3 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. 630 mg (82%) of (Z)-2-methoxy-3-[3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylic acid are obtained in the form of a white solid with a melting point of 144° 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-bd83e36353a24d60b34f2a12874c5ca3
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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