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

HRID 723916ノート

反応式

HRID 723916 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-0c7373c4592b4fe391c39cf8002042b7
出典データセット
uspto-grants-2006_11
特許番号
US07141588B2

反応ノート

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