تفاعل #2848

معادلة التفاعل

N-methyl piperidine

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

trichloroethyl chloroformate

→

title compound

المردود 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

المردود 75.0%

المذيبات

CH2Cl2 DMF

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلThe organic layer is washed with 1N HCl, H2O, saturated NaCl
2. 2
   تجفيفThe organic layer is dried over MgSO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue is purified by column chromatography
6. 6
   غسيلeluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

الإجراء التجريبي

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.

المصدر