Ammonia → (5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxamide

HRID 896192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896192
C[O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([F:21])[CH:20]=2)[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]3)[CH2:6]1)=O.[NH3:24]>CO>[F:21][C:19]1[CH:20]=[C:11]([N:7]2[CH2:6][C@H:5]([C:3]([NH2:24])=[O:2])[O:9][C:8]2=[O:10])[CH:12]=[C:13]2[C:18]=1[N:17]([CH3:22])[C:16](=[O:23])[CH2:15][CH2:14]2

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 68491736(5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

Produkt 1

HCID 10149614(5R)-3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester (Step 5, 0.300 g, 9.31 mmol) is dissolved in 2M ammonia in methanol solution (8 ml) and stirred overnight at room temperature. The resulting precipitate is filtered, washed with methanol, and dried under vacuum to give the title compound as a white solid (0.185 g, 65%), mp 260-2° C.; 1H NMR (300 MHz, CDCl3) δ 2.48-2.52 (m, 2H), 2.85-2.89 (m, 2H), 3.28 (d, 3H), 4.00 (dd, 1H), 4.24 (t, 1H), 5.03 (dd, 1H), 7.27 (s, 1H), 7.46 (dd, 1H), 7.62 (br s, 1H), 7.87 (br s, 1H); MS for C14H14FN3O4 m/z 308 (M+H)+.

Aufarbeitung

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with methanol
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-141177f1570f47f2bc6e9632946a8cd6
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919329B2

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