Sodium Hydroxide → HCID 16224816, compound

HRID 390655Notes

Reaction equation

HRID 390655 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH3:19])/[C:14]([O:16]CC)=[O:15])[CH:9]=[CH:8][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:37])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:28])[CH:21]=1)[CH3:4]>C(O)C.C(OCC)C.CCCCC>[CH2:3]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH3:19])/[C:14]([OH:16])=[O:15])[CH:9]=[CH:8][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:37])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:28])[CH:21]=1)[CH3:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86626103HCID 86626103, compound

Product 1

HCID 16224816HCID 16224816, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
50 °C

Procedure

297 mg (7.4 mmol) of sodium hydroxide are added to a solution of 357 mg (0.74 mmol) of ethyl (E)-3-[2-ethoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate in 15 mL of ethanol. The reaction mixture is heated at 50° C. for 3 hours. After cooling, the medium is evaporated to dryness, taken up in water, acidified with 2 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water, dried over magnesium sulfate and filtered. The solvent is evaporated off and the solid obtained is taken up in a mixture of ethyl ether and pentane, filtered and dried. 250 mg (75%) of (E)-3-[2-ethoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylic acid are obtained in the form of a white powder with a melting point of 123° C.

Workup

  1. temperatureAfter cooling
  2. customthe medium is evaporated to dryness
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is evaporated off
  8. customthe solid obtained
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-4296735d85ea4f8cb7a7f29a4746fda3
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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