Potassium Carbonate → HCID 24821476, compound
Reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:24][CH2:23][C:22]([O:28][P:29](=[O:32])([OH:31])[OH:30])([CH2:25][O:26][CH3:27])[CH2:21][CH2:20]3)=[C:14]([F:33])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+:38].[K+]>>[K+:38].[K+:38].[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:24][CH2:23][C:22]([O:28][P:29](=[O:30])([O-:31])[O-:32])([CH2:25][O:26][CH3:27])[CH2:21][CH2:20]3)=[C:14]([F:33])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]Participants
3
Conditions
- Temperature
- 7.5 °C
Procedure
To a solution of phosphoric acid mono-(1-{4-[(S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluoro-phenyl}-4-methoxymethyl-piperidin-4-yl) ester (5.0g, 0.010mol) anhydrous methanol (50 ml) at 0-5° C., under argon, was added anhydrous potassium carbonate (1.38 gm, 0.010 mol). The reaction mixture was stirred at 5-10° C. for 2 hours. The ice-bath was removed and the stirring continued further at 30-35° C. for 1 hour. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. Acetone (25 ml) was added to the residue and triturated. The solvent was decanted. This procedure was repeated twice with acetone (50 ml). Acetone after the third trituration was decanted and the residue dried under reduced pressure to obtain the product as white solid, 5.1 g, in 89% yield, Mp>165° C. (dec); MF: C19H24F2Na2N3O8P. Aqueous solubility at pH 7 was >200 mg/ml.