Acetic Acid → 3-[3'-(3-Heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoic acid

HRID 250857Notes

Reaction equation

HRID 250857 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][C:21]=2[O:32][CH3:33])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O.C(O)(=O)C>O1CCCC1.CO>[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][C:21]=2[O:32][CH3:33])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67272737Methyl 3-[3'-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoate

Product 1

HCID 116762523-[3'-(3-Heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoic acidYield 42%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

200 mg (5.0 mmol, 4.2 eq) of sodium hydroxide are added to a solution of 525 mg (1.19 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoate in 6 ml of a tetrahydrofuran/methanol mixture (8/2). The reaction mixture is stirred at room temperature for 3 hours. The reaction medium is hydrolyzed with water, acidified with acetic acid solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate). The product is crystallized from pentane and 216 mg of 3-[3′-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=100-101° C.). Yield=42%

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate)
  6. customThe product is crystallized from pentane and 216 mg of 3-[3′-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoic acid

Sources & evidence

ORD record
ord-3ab28213555c4d9a8550aa3fbc606307
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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