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

HRID 1095998Notes

Reaction equation

HRID 1095998 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:34])[C:20]([OH:33])([C:25]3[CH:26]=[N:27][C:28]([O:31]C)=[CH:29][CH:30]=3)[C:21]([F:24])([F:23])[F:22])=[C:15]([Cl:35])[CH:14]=2)[CH:9]=[CH:10][C:11]=1[Cl:12])=[O:5])C.Cl.[OH-].[Na+]>O1CCOCC1.O1CCCC1.CO>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:34])[C:20]([OH:33])([C:25]3[CH:30]=[CH:29][C:28](=[O:31])[NH:27][CH:26]=3)[C:21]([F:24])([F:23])[F:22])=[C:15]([Cl:35])[CH:14]=2)=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 666989914,3'-Dichloro-4'-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 666990614,3'-Dichloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In analogy to Example 175, step 6, 4,3′-dichloro-4′-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-3-carboxylic acid ethyl ester (Example 180) 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)=484.1 [M−H+].

Sources & evidence

ORD record
ord-d67880874719444aa7769c2d9ed637b3
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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