Sodium Hydroxide → (E)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylic acid

HRID 390661Notes

Reaction equation

HRID 390661 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH3:21])/[C:16]([O:18]CC)=[O:17])[CH:11]=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:37])[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6]>C(O)C.O1CCCC1>[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH3:21])/[C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:37])[C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:30])[CH:23]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86626104ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylate

Product 1

HCID 16224818(E)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

40 mg (1 mmol) of sodium hydroxide are added to a solution of 526 mg (1.1 mmol) of ethyl (E)-3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylate in 1 mL of ethanol and 10 mL of tetrahydrofuran. The reaction mixture is heated at 50° C. for 24 hours. The reaction medium is evaporated to dryness, taken up in water and acidified with aqueous 2 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture and then precipitated from heptane. 310 mg (91%) of (E)-3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-methylacrylic acid are obtained in the form of a white solid with a melting point of 87-89° C.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated off
  7. customthe oil obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 60/40 heptane/ethyl acetate mixture
  10. customprecipitated from heptane

Sources & evidence

ORD record
ord-b935f78b33e84871b4e36a519cd82fb4
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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