Water → 3-(3'-{3-[2-(4-Fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoic acid

HRID 250829Notes

Reaction equation

HRID 250829 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:34])[N:14]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[CH3:15])=[CH:6][CH:5]=1.O1CCCC1.CO.O>C(O)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:34])[N:14]([C:16]2[CH:17]=[C:18]([C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)[CH:19]=[CH:20][CH:21]=2)[CH3:15])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67272001Methyl 3-(3'-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoate

Product 1

HCID 580890803-(3'-{3-[2-(4-Fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

200 mg (5 mmol, 10 eq) of sodium hydroxide are added to a solution of 221 mg (0.51 mmol, 1 eq) of methyl 3-(3′-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoate in 6 ml of an 8/2 tetrahydrofuran/methanol mixture. The reaction mixture is stirred for 3 hours at room temperature. The reaction is stopped by addition of 10 mL of water and 2 mL of acetic acid and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 180 mg of 3-(3′-{3-[2-(4-fluorophenyl)ethyl]-1-methylureido}biphenyl-4-yl)propanoic acid are obtained (m.p.=146° C.). Yield=84%

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5e7f5f2dce8d49abb997ca636a051763
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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