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Water → Trifluoroacetic acid

HRID 70710
Notes
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Reaction equation

HRID 70710 reaction equation
CS(O)(=O)=O.[CH:6]1([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:28])[C:17]3[NH:22][C:21](=[O:23])[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:7]1.[OH2:29].[CH:30]1([OH:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[F:25][C:24]([F:27])([F:26])[C:20]([OH:35])=[O:29].[CH:30]1([O:28][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([S:9][CH:6]3[CH2:8][CH2:7]3)=[CH:11][CH:12]=2)[C:17]2[NH:22][C:21](=[O:23])[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 7298CyclopentanolHCID 67398402HCID 67398402, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 58452349HCID 58452349, compound

Conditions

Temperature
100 °C

Procedure

Methanesulfonic acid (250 μL) was added to a solution of 6-{[4-(cyclopropylsulfanyl)phenyl](hydroxy)methyl}-3-(trifluoromethyl)pyridin-2(1H)-one (40 mg) in cyclopentanol (500 μL), and the mixture was stirred at 100° C. for six hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate: 20 mL/min, eluent: A=acetonitrile, B=0.1% trifluoroacetic acid solution, gradient: 10 to 90%) to give the title compound as a colorless amorphous (25 mg, 52%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate

Sources & evidence

ORD record
ord-a623100dd4d94b999e66e38e1e60cfaa
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes