Hydrochloric Acid → HCID 54500756, compound

HRID 1740493Notes

Reaction equation

HRID 1740493 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[C:29]3[CH:30]=[CH:31][C:32](O)=[CH:33][C:28]=3[O:27][CH:26]=2)[CH2:20]1.Cl>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:32]1[CH:31]=[CH:30][C:29]2[C:25]([N:21]3[CH2:20][C@H:19]([CH2:18][O:17][CH3:16])[O:23][C:22]3=[O:24])=[CH:26][O:27][C:28]=2[CH:33]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 15381150HCID 15381150, compound

Product 1

HCID 54500756HCID 54500756, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.8 ml (0.035 mol) of trifluoromethanesulphonic anhydride are added slowly to a solution, maintained at -20° C., of 7.6 g (0.029 mol) of (R)-5-(methoxymethyl)-3-(6-hydroxybenzofuran-3-yl)oxazolidin-2-one in 60 ml of pyridine. After returning to room temperature, the mixture is poured into ice and is brought to a pH of 6 by means of 2N hydrochloric acid. The product is then extracted with ethyl acetate, the solvent is evaporated under reduced pressure and the product is purified by chromatography on silica gel with a 10/90 mixture of cyclohexane and dichloromethane.

Workup

  1. customAfter returning to room temperature
  2. additionthe mixture is poured into ice
  3. extractionThe product is then extracted with ethyl acetate
  4. customthe solvent is evaporated under reduced pressure
  5. customthe product is purified by chromatography on silica gel with a 10/90 mixture of cyclohexane and dichloromethane

Sources & evidence

ORD record
ord-0449bb5862384ee4875dbae51f03aa08
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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