Sodium Hydroxide → 1-[(3'-Chloro-2',6'-difluoro-6,4'-dimethoxy-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid

HRID 1475776Notes

Reaction equation

C[O:2][C:3]([C:5]1([NH:12][C:13]([C:15]2[CH:16]=[C:17]([C:23]3[C:28]([F:29])=[CH:27][C:26]([O:30][CH3:31])=[C:25]([Cl:32])[C:24]=3[F:33])[C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[O:14])[CH2:10][CH2:9][CH:8]([CH3:11])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].O1CCOCC1>O>[Cl:32][C:25]1[C:24]([F:33])=[C:23]([C:17]2[C:18]([O:21][CH3:22])=[CH:19][CH:20]=[C:15]([C:13]([NH:12][C:5]3([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH:8]([CH3:11])[CH2:7][CH2:6]3)=[O:14])[CH:16]=2)[C:28]([F:29])=[CH:27][C:26]=1[O:30][CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

150 mg of 1-[(3′-Chloro-2′,6′-difluoro-6,4′-dimethoxy-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic acid methyl ester and 25 mg NaOH were dissolved using 5 ml of dioxane and 0.5 ml of water. The mixture was stirred at 80° C. for 6 h. Then, 15 ml of water were added, the dioxane evaporated and acidified to pH=3 using aqueous NaHSO4-solution. The mixture was stirred for 30 minutes at room temperature. The product was then isolated by filtration and dried in vacuo to yield 110 mg of the title compound.

Workup

customthe dioxane evaporated
stirringThe mixture was stirred for 30 minutes at room temperature
customThe product was then isolated by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-436ca1d70e3b4198a821f684ab7325f0
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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