Trifluoroacetic acid → 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid

HRID 1293182

Reaktionsgleichung

Reaktionsgleichung von HRID 1293182
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:23]([NH:25][C@H:26]([C:28]2[CH:40]=[CH:39][C:31]([C:32]([O:34]C(C)(C)C)=[O:33])=[CH:30][CH:29]=2)[CH3:27])=[O:24])[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:13][CH:14]=1>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([C:23]([NH:25][C@H:26]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:39][CH:40]=2)[CH3:27])=[O:24])[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 69050742tert-butyl 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Produkt 1

HCID 116830884-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acidAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (10 mL) was added to a solution of tert-butyl 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate (step 4, 2.1 g; 4.3 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature until the starting material was fully consumed (4 h). The solvent and most of the trifluoroacetic acid were removed under reduced pressure. The residue was purified by flush silica gel column chromatography on silica gel (50 g) eluting with dichloromethane/methanol (20/1) and recrystallization (ethyl acetate-diisopropyl ether) to give 1.24 g, (86%) of the title compounds as white crystals: mp 198.2° C.;

Aufarbeitung

  1. customwas fully consumed (4 h)
  2. customThe solvent and most of the trifluoroacetic acid were removed under reduced pressure
  3. customThe residue was purified
  4. customby flush silica gel column chromatography on silica gel (50 g)
  5. washeluting with dichloromethane/methanol (20/1) and recrystallization (ethyl acetate-diisopropyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-3ffa0587373041ac814809117247c12c
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238714B2

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