Reaktion #10399

Reaktionsgleichung

2-cyclopropylamino-4,5-difluorobenzoic acid

tert-butyl carbazate

1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide

→

N2-(2-cyclopropylamino-4,5-difluorobenzoyl)hydrazinecarboxylic acid tert-butyl ester

Ausbeute 81.4%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated NaHCO3, water, and brine
2. 2
   TrocknenThe organic layer is dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   EinengenThe filtrate is concentrated under vacuum
5. 5
   Sonstigepurified via flash column chromatography (1:2 ethyl acetate/hexanes)

Vorschrift

To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5) (1.32 g, 6.19 mmol) and tert-butyl carbazate (1.30 g, 9.75 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (1.87 g, 9.75 mmol). After 16 hours, the reaction mixture is diluted with dichloromethane and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (1:2 ethyl acetate/hexanes) to afford N2-(2-cyclopropylamino-4,5-difluorobenzoyl)hydrazinecarboxylic acid tert-butyl ester as a solid (1.65 g). MS EI: m/z 328 (M+).

Quelle