Acetic Acid → (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acid

HRID 390590Notes

Reaction equation

HRID 390590 reaction equation
[OH-].[Li+].[CH2:3]([O:5]/[C:6](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)/[C:7]([O:9]CC)=[O:8])[CH3:4].C(O)(=O)C.O>O1CCCC1.C(OCC)(=O)C>[CH2:3]([O:5]/[C:6](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:36])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)/[C:7]([OH:9])=[O:8])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 16224918ethyl (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate

Product 1

HCID 16225328(Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acidYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
68 °C

Procedure

0.93 mL (0.93 mmol) of aqueous 1 M lithium hydroxide solution is added to a solution of 0.29 g (0.62 mmol) of ethyl (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate in 8 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 18 hours. After cooling, the reaction is worked up by addition of 0.93 mL (0.93 mmol) of aqueous 1 M acetic acid solution and 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. After filtration, the solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture to give 0.10 g (37%) of (Z)-2-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylic acid in the form of a white solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvents are evaporated off
  6. customThe crude product obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 60/40 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-8547d856cdb8409bb12efb9f291aed57
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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