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

HRID 723916Notes

Reaction equation

HRID 723916 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-0c7373c4592b4fe391c39cf8002042b7
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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