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Pyridine → 2-(4-Chloro-3-fluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester

HRID 1987580
Notes
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Reaction equation

HRID 1987580 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[CH2:13]([O:15][C:16](=[O:28])[CH:17]([NH2:27])[CH:18]([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])[CH3:14].N1C=CC=CC=1>ClC(Cl)C>[CH2:13]([O:15][C:16](=[O:28])[CH:17]([NH:27][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:12])[CH:4]=1)(=[O:10])=[O:9])[CH:18]([C:19]([F:22])([F:20])[F:21])[C:23]([F:25])([F:26])[F:24])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 435661924-Chloro-3-fluorobenzene-1-sulfonyl chlorideHCID 529919404,4,4,4',4',4'-Hexafluorovaline, ethyl ester

Product 1

HCID 866160062-(4-Chloro-3-fluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl esterYield 62.5%

Reagents, catalysts & solvents 1

HCID 6365
1,1-Dichloroethane
Solvent

Procedure

To a vial containing a solution of 4-chloro-3-fluorobenzenesulfonyl chloride (181 mg, 0.79 mmol) and 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (200 mg, 0.79 mmol) in anhydrous dichloroethane (3 mL) was added pyridine (192 μL). The vial was capped and shaken for 18 h. The solvent was removed in vacuo and the residue transferred to a separatory funnel with EtOAc (100 mL) and washed with distilled water (100 mL×2). The organic layer was removed and the combined aqueous washings were extracted with EtOAc (100 mL×2). The organic extracts were combined, washed with brine (100 mL), dried (MgSO4), filtered, and evaporated to give a yellow solid (220 mg). This material was adsorbed onto silica gel and purified by column chromatography, eluent: HCCl3, to afford a white solid (186 mg, 53%). Mass Spectrum (+ESI): 446 [M−H]+.

Workup

  1. customThe vial was capped
  2. customThe solvent was removed in vacuo
  3. customthe residue transferred to a separatory funnel with EtOAc (100 mL)
  4. washwashed with distilled water (100 mL×2)
  5. customThe organic layer was removed
  6. extractionthe combined aqueous washings were extracted with EtOAc (100 mL×2)
  7. washwashed with brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-29134f013d8345209cef92ed6af84489
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07550629B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes