Sodium Hydroxide → HCID 68956488, compound

HRID 390629Notes

Reaction equation

HRID 390629 reaction equation
[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[C:25](\[CH3:31])/[C:26]([O:28]CC)=[O:27])=[CH:20][C:19]=2[O:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[C:1]([CH2:9][NH:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[C:25](\[CH3:31])/[C:26]([OH:28])=[O:27])=[CH:20][C:19]=2[O:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86626089HCID 86626089, compound

Product 1

HCID 68956488HCID 68956488, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
52.5 °C

Procedure

265 mg (0.55 mmol) of ethyl (E)-3-{3′-[(benzoylmethylamino)methyl]-2-butoxybiphenyl-4-yl}-2-methylacrylate are placed in a solution of 109 mg (2.75 mmol) of sodium hydroxide in 5 mL of ethanol. After heating at 50-55° C. for 6 hours, the reaction medium is evaporated to dryness, taken up in water, acidified to pH 3 with aqueous 1 N hydrochloric 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 a 50/50 heptane/ethyl acetate mixture. 165 mg (66%) of (E)-3-{3′-[(benzoylmethylamino)methyl]-2-butoxybiphenyl-4-yl}-2-methylacrylic acid are obtained in the form of an off-white powder with a melting point of 166° C.

Workup

  1. customthe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis recrystallized from a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-cb42e746627643859fc4dd17130f723a
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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