Methanesulfonic Acid → HCID 88331612, compound

HRID 1292419Notes

Reaction equation

HRID 1292419 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[C:14]([F:25])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[CH3:26][S:27]([OH:30])(=[O:29])=[O:28]>CO>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[C:1]([NH:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]([F:25])[C:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[C:16]([F:18])[CH:17]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9863078HCID 9863078, compound

Product 1

HCID 88331612HCID 88331612, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-5-(Acetamidomethyl)3-[4-(3-pyridyl)]-3,5-difluorophenyl-2-oxazolidinone (EXAMPLE 1, 74 mg, 0.21 mmol) and methanesulfonic acid (14 μl, 0.21 mmol) are combined in methanol (4 ml). The mixture is warmed to reflux temperature for 3 min and the reaction becomes homogeneous. The reaction is cooled to 20°-25° and concentrated under reduced pressure to a solid. The solid is triturated with ether and the recovered solid is dissolved in water (8 ml), filtered and lyophilized, to give the title compound, mp 203°-205°.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureto reflux temperature for 3 min
  3. temperatureThe reaction is cooled to 20°-25°
  4. concentrationconcentrated under reduced pressure to a solid
  5. customThe solid is triturated with ether
  6. dissolutionthe recovered solid is dissolved in water (8 ml)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ec962780ea6e438b867fc27df3e2dfa2
Source dataset
uspto-grants-1998_05
Patent number
US05756732

Reaction notes

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