Pyridine → 2-(3,5-Difluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester

HRID 1987576Notes

Reaction equation

HRID 1987576 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[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>C(Cl)Cl>[CH2:13]([O:15][C:16](=[O:28])[CH:17]([NH:27][S:9]([C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)(=[O:11])=[O:10])[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 27740583,5-Difluorobenzenesulfonyl chlorideHCID 529919404,4,4,4',4',4'-Hexafluorovaline, ethyl ester

Product 1

HCID 866160032-(3,5-Difluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,5-difluoro-benzenesulfonyl chloride (252 mg, 1.19 mmol) and 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (300 mg, 1.19 mmol) in CH2Cl2 (7 mL) was added anhydrous pyridine (144 μL, 1.77 mmol, 1.50 equiv.) and the vial capped and shaken for 72 h. The reaction solution was transferred to a separatory funnel with CH2Cl2 (100 mL), washed with 1M citric acid solution (100 mL), water (50 mL×4), brine (100 mL), dried (MgSO4), filtered and evaporated to give a white solid (300 mg, 59%). Mass Spectrum (−ESI): 427.8 [M−H]−

Workup

  1. customthe vial capped
  2. washwashed with 1M citric acid solution (100 mL), water (50 mL×4), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9d72bf5b912a4308ae2db893a8025961
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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