Reacción #10399

Ecuación de reacción

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

Rendimiento 81.4%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated NaHCO3, water, and brine
2. 2
   SecadoThe organic layer is dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   ConcentraciónThe filtrate is concentrated under vacuum
5. 5
   Otropurified via flash column chromatography (1:2 ethyl acetate/hexanes)

Procedimiento

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+).

Fuente