Acetic Anhydride → HCID 69980081, compound

HRID 1167473Notes

Reaction equation

HRID 1167473 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][O:22][C:23]3[CH:27]=[CH:26][O:25][N:24]=3)[O:18][C:17]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH:13]=[N:14]O)[N:10]=[CH:9]1.C(OC(=O)C)(=O)C>>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][O:22][C:23]3[CH:27]=[CH:26][O:25][N:24]=3)[O:18][C:17]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]#[N:14])[N:10]=[CH:9]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54183277HCID 54183277, compound

Product 1

HCID 69980081HCID 69980081, compoundYield 39.3%

Procedure

3-(3-Fluoro-4-(4-hydroximinomethyl-imidazol-1-yl)phenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one (360 mg, 0.93 mmol) and acetic anhydride (3 ml) were heated under nitrogen at reflux for 2 hours. After cooling and pouring onto ice, the mixture was extracted into dichloromethane (3×15 ml). dried (magnesium sulfate) and evaporated. The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 2.5% MeOH in dichloromethane, to give the desired compound (135 mg).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling
  3. additionpouring onto ice
  4. extractionthe mixture was extracted into dichloromethane (3×15 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
  8. washeluting with a gradient
  9. temperatureincreasing in polarity from 0 to 2.5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-7917c97eb5844950b055c0d387b47505
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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