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Methanol → 6-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid

HRID 1095906
Notes
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Reaction equation

HRID 1095906 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:30])[C:17]([OH:29])([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[CH:23]=3)[C:18]([F:21])([F:20])[F:19])=[C:12]([Cl:31])[CH:11]=2)=[N:6][CH:5]=1.[Li+].[OH-].CO>C1COCC1>[Cl:31][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][N:6]=2)[CH:15]=[CH:14][C:13]=1[CH:16]([CH3:30])[C:17]([OH:29])([C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[CH:23]=1)[C:18]([F:20])([F:19])[F:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 666991666-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid methyl ester

Product 1

HCID 595085726-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To 6-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-nicotinic acid methyl ester (22 mg) aqueous 1N LiOH (5 ml), MeOH (2.5 ml) and THF (5 ml) were added. The resulting solution was stirred for 2 h at room temperature. Volatile solvents were removed in vacuo. The residual aqueous solution was diluted with water (10 ml) and washed with DCM (10 ml), then acidified to pH 6 with 1 N aqueous HCl and extracted with EtOAc. The combined EtOAc layers were dried over Na2SO4 and concentrated to give the title compound (21 mg) as a yellow oil. MS (m/e)=451.0 [M+H+].

Workup

  1. customVolatile solvents were removed in vacuo
  2. additionThe residual aqueous solution was diluted with water (10 ml)
  3. washwashed with DCM (10 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined EtOAc layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f079cf7883794a5bb70df63c6ab0c3f0
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138189B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes