Sodium Hydroxide → 3-[3'-(3-Octyl-1-methylureido)biphenyl-4-yl]propanoic acid

HRID 250838Notes

Reaction equation

HRID 250838 reaction equation
[OH-].[Na+].[CH2:3]([NH:11][C:12](=[O:34])[N:13]([C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(O)C>[CH2:3]([NH:11][C:12](=[O:34])[N:13]([C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67273465Ethyl 3-[3'-(3-octyl-1-methylureido)biphenyl-4-yl]propanoate

Product 1

HCID 115822933-[3'-(3-Octyl-1-methylureido)biphenyl-4-yl]propanoic acidYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

684 mg (17.1 mmol, 10 eq) of sodium hydroxide are added to a solution of 750 mg (1.71 mmol, 1 eq) of ethyl 3-[3′-(3-octyl-1-methylureido)biphenyl-4-yl]propanoate in 15 mL of ethanol. The reaction mixture is heated at 50° C. for 6 hours. The reaction medium is evaporated to dryness, taken up in water, acidified with 1N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the orange oil obtained is chromatographed on silica gel (30 g FlashSmart Pack column) eluted with 30/70 heptane/ethyl acetate and then crystallized from ethyl ether, filtered and dried. 500 mg of 3-[3′-(3-octyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=86-88° C.). Yield=71%

Workup

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated off
  6. customthe orange oil obtained
  7. customis chromatographed on silica gel (30 g FlashSmart Pack column)
  8. washeluted with 30/70 heptane/ethyl acetate
  9. customcrystallized from ethyl ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-94d0f045fe4c42a69c6d2554ece07f23
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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