Acetic Acid → HCID 16225216, compound

HRID 390690Notes

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

Participants

Conditions

Temperature: 68 °C

Procedure

3.3 mL (3.3 mmol) of aqueous 1 N sodium hydroxide solution are added to a solution of 1 g (2.2 mmol) of methyl (Z)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylate in 16 mL of tetrahydrofuran. The reaction medium is heated at 68° C. and stirred for 4 hours. The reaction medium is acidified with 3.5 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 a hot heptane/ethyl acetate mixture. 800 mg (86%) of (Z)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the form of a white solid with a melting point of 114° 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 a hot heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-4c8e84ec18d547c2b5e4af6671900218
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383652B2

Reaction notes

Loading…