Ammonia → (5R)-3-(4-Fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxamide
Reaction equation
[NH3:1].[F:2][C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[O:11][C:7]=2[CH:6]=[C:5]([N:14]2[CH2:18][C@H:17]([C:19](OC)=[O:20])[O:16][C:15]2=[O:23])[CH:4]=1>CO>[F:2][C:3]1[C:8]2[N:9]([CH3:13])[C:10](=[O:12])[O:11][C:7]=2[CH:6]=[C:5]([N:14]2[CH2:18][C@H:17]([C:19]([NH2:1])=[O:20])[O:16][C:15]2=[O:23])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ammonia in methanol (2M, 5 ml) is added to solid methyl (5R)-3-(4-fluoro-3-methyl-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-1,3-oxazolidine-5-carboxylate (Step 9, 0.250 g, 0.806 mmol) and the suspension stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure and the residue purified by PTLC (10% methanol/dichloromethane) to give product as a white solid (0.13 g, 55%); MS for C12H10FN3O5 m/z 296 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 7.87 (br s, 1H), 7.63 (br s, 1H), 7.50 (d, 1H), 7.42 (dd, 1H), 5.03 (dd, 1H), 4.26 (t, 1H), 4.01 (dd, 1H), 3.42 (s, 3H).