Reaktion #2848

Reaktionsgleichung

N-methyl piperidine

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

trichloroethyl chloroformate

→

title compound

Ausbeute 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

Ausbeute 75.0%

Lösungsmittel

CH2Cl2 DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer is washed with 1N HCl, H2O, saturated NaCl
2. 2
   TrocknenThe organic layer is dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue is purified by column chromatography
6. 6
   Wascheneluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Vorschrift

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.

Quelle