Sodium Methoxide → HCID 24821475, compound

HRID 2064099Notes

Reaction equation

HRID 2064099 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-].[Na+:36]>>[Na+:36].[Na+:36].[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 10942334Sodium MethoxideHCID 24763648HCID 24763648, compound

Product 1

HCID 24821475HCID 24821475, compoundYield 92%

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-difluorophenyl}-4-methoxymethyl-piperidin-4-yl) ester (5.0 g, 0.010 mol) anhydrous methanol (50 ml) at 0-5° C., under argon, was added anhydrous sodium methoxide powder (0.542 g, 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 off-white solid, 5.0 g, in 92% yield, Mp>150° C. (dec); MF: C19H24F2K2N3O8P. 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-b0bc9ad60a8648a39773b2dc7a1e43a7
Source dataset
uspto-grants-2012_10
Patent number
US08288416B2

Reaction notes

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