Acetic Acid → HCID 16223526, compound

HRID 390620Notes

Reaction equation

[OH-].[Na+].[CH3:3][O:4]/[C:5](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:35])[C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:25])[CH:18]=2)=[CH:13][CH:12]=1)/[C:6]([O:8]C)=[O:7].C(O)(=O)C>O1CCCC1>[CH3:3][O:4]/[C:5](=[CH:10]\[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:35])[C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:25])[CH:18]=2)=[CH:15][CH:16]=1)/[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 68 °C

Procedure

1.7 mL (1.7 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 0.5 g (1.1 mmol) of methyl (Z)-2-methoxy-3-[3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]acrylate in 10 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 4 hours. The reaction medium is acidified with 2 mL of 1 N acetic acid solution and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is recrystallized from hot ethyl acetate. 500 mg (71%) of (Z)-2-methoxy-3-[3′-(1-methyl-3-phenethylureido)biphenyl-4-yl]acrylic acid are obtained in the form of a white solid with a melting point of 144° C.

Workup

extractionextracted with ethyl acetate
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue obtained
customis recrystallized from hot ethyl acetate

Sources & evidence

ORD record: ord-4fb0cc12257f4af6b5ecbf6cb1b10983
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383652B2

Reaction notes

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