Potassium Carbonate → HCID 24821476, compound

HRID 2064100Notes

Reaction equation

HRID 2064100 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

Reactant 2

HCID 11430Potassium CarbonateHCID 24763648HCID 24763648, compound

Product 1

HCID 24821476HCID 24821476, compoundYield 89%

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.

Workup

  1. customThe ice-bath was removed
  2. waitthe stirring continued further at 30-35° C. for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. additionAcetone (25 ml) was added to the residue
  6. customtriturated
  7. customThe solvent was decanted
  8. customAcetone after the third trituration was decanted
  9. customthe residue dried under reduced pressure

Sources & evidence

ORD record
ord-92da3b9fc1ea401896ca590ca8f98d5e
Source dataset
uspto-grants-2012_10
Patent number
US08288416B2

Reaction notes

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