Reacción #2848

Ecuación de reacción

N-methyl piperidine

3-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate

trichloroethyl chloroformate

→

title compound

Rendimiento 75.0%

([3-[3-(S)-(4,6-Dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-phenyl]-iminomethyl)-carbamic acid 2,2.2-trichloroethyl ester

Rendimiento 75.0%

Disolventes

CH2Cl2 DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic layer is washed with 1N HCl, H2O, saturated NaCl
2. 2
   SecadoThe organic layer is dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue is purified by column chromatography
6. 6
   Lavadoeluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Procedimiento

To a solution of 3-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate (0.25 g, 0.40 mmol), prepared as in EXAMPLE 14, Part E, in 4 mL of CH2Cl2 :DMF (10:1) is added N-methyl piperidine (0.12 g, 1.2 mmol) followed by trichloroethyl chloroformate (0.93 g, 0.44 mmol). The solution is stirred for 16 h. After this time, the solution is diluted with EtOAc. The organic layer is washed with 1N HCl, H2O, saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (0.20 g, 0.30 mmol) as a white solid.

Fuente