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

HRID 723916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723916
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-0c7373c4592b4fe391c39cf8002042b7
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141588B2

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