Hydrochloric Acid → 3'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-4-biphenylcarboxylic acid

HRID 2426781Notes

Reaction equation

[OH-].[Na+].[O:3]=[C:4]1[NH:8][C:7](=[O:9])[O:6][N:5]1[CH2:10][C:11]1[CH:34]=[CH:33][C:14]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31]C)=[O:30])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1.CO.Cl>C1COCC1>[O:3]=[C:4]1[NH:8][C:7](=[O:9])[O:6][N:5]1[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 1 M sodium hydroxide aqueous solution (5 ml) was added to a mixture of methyl 3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-4-biphenylcarboxylate (196 mg), methanol (5 ml) and THF (5 ml), followed by stirring for 1 hour with heating at 60° C. A 1 M hydrochloric acid (7 ml) was added to the reaction mixture, followed by stirring at room temperature. The solid precipitated was collected by filtration and dried by heating under a reduced pressure to obtain 3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-4-biphenylcarboxylic acid (176 mg) as a white solid.

Workup

stirringby stirring at room temperature
customThe solid precipitated
filtrationwas collected by filtration
customdried
temperatureby heating under a reduced pressure

Sources & evidence

ORD record: ord-d8a3523866b94c90814bce77fb2ab060
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968552B2

Reaction notes

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