Acetic Acid → HCID 16225332, compound

HRID 390600Notes

Reaction equation

HRID 390600 reaction equation
[OH-].[Li+].[CH2:3]([O:5]/[C:6](=[CH:12]\[C:13]1[CH:14]=[N:15][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])[CH:20]=2)=[CH:17][CH:18]=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:14]=[N:15][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])[CH:20]=2)=[CH:17][CH:18]=1)/[C:7]([OH:9])=[O:8])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 16225428HCID 16225428, compound

Product 1

HCID 16225332HCID 16225332, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
68 °C

Procedure

0.4 mL (0.45 mmol) of aqueous 1 M lithium hydroxide solution is added to a solution of 0.14 g (0.3 mmol) of ethyl (Z)-2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}acrylate in 6 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 24 hours. After cooling, the reaction is worked up by addition of 0.45 mL (0.45 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. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 90/10 dichloromethane/methanol mixture to give 60 mg (46%) of (Z)-2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}acrylic acid in the form of a yellow oil.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents are evaporated off
  5. customThe crude product obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 90/10 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-19d894a354a44e07bd7948d0585e1df5
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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