(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one → N-{[(5S)-3-(5-Bromopyrid-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

HRID 747203Notes

Reaction equation

HRID 747203 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]([Br:17])=[CH:13][N:12]=2)[CH2:6]1)=[N+]=[N-].[C:18]([OH:21])(=S)[CH3:19]>>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][NH:1][C:18](=[O:21])[CH3:19])[O:9][C:8]2=[O:10])=[N:12][CH:13]=1

Participants

3

Reactant 2

HCID 15341129(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-oneHCID 178418634HCID 178418634, compound

Product 1

HCID 15341123N-{[(5S)-3-(5-Bromopyrid-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

Procedure

(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one (5.60 g, 18.7 mM) was dissolved in thioacetic acid (10 ml) to give a yellow solution. The solution was degassed and stirred at room temperature for 20 hours. The thick slurry was concentrated and the desired product was crystallized from acetone (100 ml) to give the product as a light yellow solid (3.25 g).

Workup

  1. customto give a yellow solution
  2. customThe solution was degassed
  3. concentrationThe thick slurry was concentrated
  4. customthe desired product was crystallized from acetone (100 ml)

Sources & evidence

ORD record
ord-0ba4f557d7a0472f9a35f613d8916c97
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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