Hydrochloric Acid → 3'-Chloro-3-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-carboxylic acid

HRID 1095994Notes

Reaction equation

HRID 1095994 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]([CH3:32])[C:18]([OH:31])([C:23]3[CH:24]=[N:25][C:26]([O:29]C)=[CH:27][CH:28]=3)[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:33])[CH:12]=2)=[CH:7][C:6]=1[F:34])=[O:4].Cl.[OH-].[Na+]>O1CCOCC1.O1CCCC1.CO>[Cl:33][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([F:34])[CH:7]=2)[CH:16]=[CH:15][C:14]=1[CH:17]([CH3:32])[C:18]([OH:31])([C:23]1[CH:28]=[CH:27][C:26](=[O:29])[NH:25][CH:24]=1)[C:19]([F:22])([F:21])[F:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 666991123'-Chloro-3-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 666991503'-Chloro-3-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In analogy to Example 175, step 6, 3′-chloro-3-fluoro-4′-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-carboxylic acid methyl ester (Example 176) was treated first with aqueous HCl in dioxane, followed by aqueous NaOH in tetrahydrofuran/methanol to give the title compound as a colorless solid. MS (m/e, ISP neg. ion)=468.1 [M−H+].

Sources & evidence

ORD record
ord-3869a2883c68444aa4a9603d4762c388
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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