Hydrochloric Acid → 3-Fluoro-4'-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

HRID 1617641Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=[O:20])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[F:36])=[O:4].[Li+].[OH-].Cl>C1COCC1.CO>[F:36][C:6]1[CH:7]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=[O:20])=[CH:15][CH:16]=2)[CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-fluoro-4′-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester (35 mg) in THF (0.2 ml) and MeOH (0.2 ml) was added a 1M aqueous LiOH solution (0.145 ml) at 0° C. The mixture was stirred at 0° C. for 30 min and at room temperature for 1 h. Since the reaction was not finished, 1 M aqueous LiOH solution (0.435 ml) was added portionwise while stirring for another 24 h at room temperature. The reaction mixture was acidified using 1 M HCl. The organic solvents were removed under vacuum. The precipitated solid was collected by filtration, washed with water and dried to give the title compound (29 mg) as a colorless solid, MS (ESI−): m/z=468.2 [M−H]−.

Workup

stirringwhile stirring for another 24 h at room temperature
customThe organic solvents were removed under vacuum
filtrationThe precipitated solid was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-1256ef46db6c4f18b609526b63d05cb2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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