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

HRID 250840Notes

Reaction equation

[OH-].[Na+].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:36])[N:15]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH3:16])=[CH:9][CH:8]=1)[CH2:4][CH2:5][CH3:6]>C(O)C>[CH2:3]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:36])[N:15]([C:17]2[CH:18]=[C:19]([C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=3)[CH:20]=[CH:21][CH:22]=2)[CH3:16])=[CH:11][CH:12]=1)[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 50 °C

Procedure

380 mg (10 mmol, 10 eq) of sodium hydroxide are added to a solution of 436 mg (1.0 mmol, 1 eq) of ethyl 3-{3′-[3-(4-butylphenyl)-1-methylureido]biphenyl-4-yl}propanoate in 20 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, 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 352 mg of 3-{3′-[3-(4-butylphenyl)-1-methylureido]biphenyl-4-yl}propanoic acid are obtained in the form of white crystals (m.p.=157-158° C.). Yield=86%

Workup

customThe reaction medium is evaporated to dryness
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
customThe solvent is evaporated off

Sources & evidence

ORD record: ord-2d4153434b7b4684a3f979ce544eb444
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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