Reaktion #970033

Reaktionsgleichung

IBX

2-iodoxybenzoic acid

tert-butyl 1-benzyl-2-(3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoyl)-hydrazinecarboxylate

NaHCO3

water

→

title compound

Ausbeute 85.1%

tert-butyl 1-Benzyl-2-(3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-oxo-4-phenylbutanoyl)hydrazinecarboxylate

Ausbeute 85.1%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with EtOAc
2. 2
   Waschenthe combined organic layers were washed with saturated aqueous NaHCO3 solution, water
3. 3
   Trocknendried (MgSO4)
4. 4
   SonstigePurification by flash column chromatography (gradient 1-10% MeOH in DCM)

Vorschrift

IBX (189 mg, 0.303 mmol, 45 wt %) was added a solution of tert-butyl 1-benzyl-2-(3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoyl)-hydrazinecarboxylate (130 mg, 0.216 mmol) in DMSO (3 mL). After stiffing overnight saturated aqueous NaHCO3 solution (15 mL) and water (15 mL) were added. The mixture was extracted with EtOAc, the combined organic layers were washed with saturated aqueous NaHCO3 solution, water and dried (MgSO4). Purification by flash column chromatography (gradient 1-10% MeOH in DCM) provided the title compound (110 mg, 85%).

Quelle