Trifluoroacetic acid → HCID 178509553, Verbindung

HRID 1424158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424158
C(OC(=O)[NH:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10](=[O:31])[NH:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10]([NH2:11])=[O:31]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 178454216HCID 178454216, Verbindung

Produkt 1

HCID 178509553HCID 178509553, VerbindungAusbeute 66,3 %

Versuchsvorschrift

(S)-tert-butyl(1-(5-(4-cyano-3-fluorophenyl)-1H-benzo[d]imidazol-2-yl)-3-oxo-3-(tritylamino)propyl)carbamate (Preparation 17, 28 mg, 0.042 mmol) was dissolved in trifluoroacetic acid (1.1 mL, 14 mmol) and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, azeotroped with methanol (3×), and purified by silica gel column chromatography eluting with 0-100% CMA80/methylene chloride to afford the title compound (9 mg, 37%) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with methanol (3×)
  3. custompurified by silica gel column chromatography
  4. washeluting with 0-100% CMA80/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-ddb9fd82344545c9b19338ee666bae09
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927587B2

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