Trifluoroacetic acid → N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide

HRID 1058247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058247
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][CH:32]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH:33]([F:35])[F:34])=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][CH:32]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH:33]([F:35])[F:34])=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 69939378HCID 69939378, Verbindung

Produkt 1

HCID 69938780N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamideAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (5.3 mL) was added to a stirred solution of N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-1-tert-butoxycarbonyl-L-prolinamide (0.626 g, 1.20 mmol) in CH2Cl2 (5.3 mL). After 1 h the solvent was evaporated in vacuo and the residue was partitioned between EtOAc and saturated aqueous Na2CO3. The EtOAc layer was dried (Na2SO4) and evaporated in vacuo to give N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.439 g) as a foam; MS m/z=438.4.

Aufarbeitung

  1. customAfter 1 h the solvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous Na2CO3
  3. dry with materialThe EtOAc layer was dried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-756ca97785144ad289cbe2e50156ced8
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515011B2

Notizen zur Reaktion

Wird geladen…