Sodium Hydroxide → HCID 16224817, compound

HRID 390659Notes

Reaction equation

HRID 390659 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH2:19][CH3:20])/[C:14]([O:16]CC)=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:38])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH:22]=1)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH2:19][CH3:20])/[C:14]([OH:16])=[O:15])[CH:9]=[CH:8][C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:38])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH:22]=1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68960214HCID 68960214, compound

Product 1

HCID 16224817HCID 16224817, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

249 mg (6.2 mmol) of sodium hydroxide are added to a solution of 616 mg (0.65 mmol) of ethyl 2-[1-[2-ethoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate in 15 mL of ethanol. The reaction mixture is heated at 50° C. for 3 hours. The reaction medium is evaporated to dryness, taken up in water and extracted with ethyl acetate. The aqueous phase is 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. The solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/ethyl acetate mixture. 222 mg (77%) of 2-[1-[2-ethoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyric acid are obtained in the form of a yellowish oil.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is evaporated off
  7. customthe oil obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-0fba6c224933421e9a941df5b3e34225
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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