Réaction #795649

Équation de réaction

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

→

title compound

Rendement 76.2%

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

Rendement 76.2%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Filtrationthe reaction mixture was filtered through a pad of celite with THF
2. 2
   Lavagewash (250 mL)
3. 3
   ConcentrationThe filtrate was concentrated
4. 4
   Autrethe residue was purified via silica gel chromatography (MeOH-DCM, 0-5%)

Mode opératoire

To a solution of benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (1.8 g, 2.57 mmol) in THF (21 ml) was added MnO2 (4.9 g, 56.5 mmol). After stirring at rt for 20 h, the reaction mixture was filtered through a pad of celite with THF wash (250 mL). The filtrate was concentrated, and the residue was purified via silica gel chromatography (MeOH-DCM, 0-5%) to afford the title compound (1.4 g, 76%). LCMS: Rt=1.04 min, m/z=715.3 (M+H). Method 2m_acidic.

Source