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Hydrochloric Acid → 3-[6-(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionic acid

HRID 2080434
Notes
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Reaction equation

HRID 2080434 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[N:16]=[C:15]([CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[C:14]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:13][C:12]=2[F:32])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[N:16]=[C:15]([CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[C:14]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:13][C:12]=2[F:32])(=[O:10])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23114759Methyl 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionate

Product 1

HCID 671017493-[6-(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To an ethanol (8 ml) solution of methyl 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionate (387 mg, 0.80 mmol) was added a 1N aqueous sodium hydroxide solution (4 ml). The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was acidified with 1N hydrochloric acid, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with a mixed solvent of diethyl ether and hexane and then collected by filtration to give the title compound (349 mg, 0.74 mmol, 93%) as a white solid.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. washwas washed with a mixed solvent of diethyl ether and hexane
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f4e1ba523afc4d20a860c8edcf526b77
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932271B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes