(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one → (S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

HRID 459018Notes

Reaction equation

HRID 459018 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[CH:12]=2)[CH2:6]1)=[N+]=[N-].[C:19]([OH:22])(=S)[CH3:20]>>[F:18][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][NH:1][C:19](=[O:22])[CH3:20])[O:9][C:8]2=[O:10])[CH:16]=[CH:15][C:14]=1[I:17]

Participants

3

Reactant 2

HCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one2×HCID 178418634HCID 178418634, compound

Product 1

HCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

Procedure

(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one (Intermediate 5, 5.00 g, 0.014 mol) was suspended in thioacetic acid (10 ml) and the solution was stirred under nitrogen at room temperature for ca. 16 h. The resulting suspension was concentrated under vacuum. The crude product was crystallized from methanol/acetone, then further purified by chromatography on silica gel using dichloromethane to give 3.71 g of the title product as a white solid.

Workup

  1. concentrationThe resulting suspension was concentrated under vacuum
  2. customThe crude product was crystallized from methanol/acetone
  3. customfurther purified by chromatography on silica gel

Sources & evidence

ORD record
ord-936995ba37c8491db0aa450d58d1a383
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

Loading…