Réaction #795662

Équation de réaction

benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2S,3S)-2-(((methylsulfonyl)oxy)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate

NaI

sodium azide

→

title compound

Rendement 57.3%

Benzhydryl 1-(((Z)-(2-(((2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate

Rendement 57.3%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrethe reaction mixture was quenched with ice cold water
2. 2
   Extractionextracted with EtOAc
3. 3
   LavageCombined organic layers were washed with water, brine
4. 4
   Séchagedried over anhydrous Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude residue was purified via silica gel chromatography (EtOAc-heptane)

Mode opératoire

To a solution of benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2S,3S)-2-(((methylsulfonyl)oxy)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (1.3 g, 1.82 mmol) in DMF (20 ml) was added NaI (0.82 g, 5.5 mmol) and sodium azide (0.83 g, 12.8 mmol). After stirring at 60° C. for 6 h, the reaction mixture was quenched with ice cold water and extracted with EtOAc. Combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-heptane) to afford the title compound (689 mg, 57%). LCMS: R=1.02 min, m/z=661.1 (M+1), Method 2m_acidic.

Source