Diisopropylethylamine → (5R)-3-(5-Bromopyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747205Notes

Reaction equation

HRID 747205 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=2)[CH2:4]1.C(N(C(C)C)CC)(C)C.Cl[CH:26](Cl)[C:27](=[N:29][NH:30]S(C1C(C)=CC=CC=1)(=O)=O)[CH3:28]>CO>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:5]2[CH2:4][C@H:3]([CH2:2][N:1]3[CH:26]=[C:27]([CH3:28])[N:29]=[N:30]3)[O:7][C:6]2=[O:8])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15341131(5S)-5-(Aminomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-oneHCID 865980671,1-Dichloroacetone toluenesulfonylhydrazone

Product 1

HCID 59749508(5R)-3-(5-Bromopyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5S)-5-(Aminomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one (4.54 g, 16.7 mM) was dissolved in methanol (100 ml). Diisopropylethylamine (5.86 g, 20.9 mM) was added and the reaction was cooled to 0° in an ice bath. Toluenesulfonic acid 2-(2,2-dichloro-1-methylethylidene)hydrazide (5.86 g, 20.9 mM) was added to give an orange solution. The reaction was stirred overnight while slowly warming to room temperature. The desired product precipitated as a yellow solid (4.10 g) and was filtered.

Workup

  1. temperaturethe reaction was cooled to 0° in an ice bath
  2. customto give an orange solution
  3. customThe desired product precipitated as a yellow solid (4.10 g)
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-7147a50a7a434dcead17bf50531ec521
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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