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

HRID 1987576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987576
[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]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 27740583,5-Difluorobenzenesulfonyl chlorideHCID 529919404,4,4,4',4',4'-Hexafluorovaline, ethyl ester

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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]−

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9d72bf5b912a4308ae2db893a8025961
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550629B2

Notizen zur Reaktion

Wird geladen…