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

HRID 1987582Notes

Reaction equation

HRID 1987582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[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]([F:1])=[C:3]([CH3:12])[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]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27827584-Fluoro-3-methylbenzene-1-sulfonyl chlorideHCID 529919404,4,4,4',4',4'-Hexafluorovaline, ethyl ester

Product 1

HCID 866160074,4,4-Trifluoro-2-(4-fluoro-3-methyl-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl esterYield 64.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a vial containing a solution of 4-fluoro-3-methylbenzenesulfonyl chloride (50 mg, 0.24 mmol) and 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (61 mg, 0.24 mmol) in anhydrous dichloroethane (1 mL) was added pyridine (58 μL, 0.719 mmol). 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 white solid (66 mg). This material was purified by Gilson RP-HPLC (column YMC Combiprep 50×20 mm, gradient 10-100% CH3CN: H2O) to afford a white solid (29 mg, 28%). Mass Spectrum (−ESI): 424 [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-b5e6f40a4747459e82954a9e0640e8f9
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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