反応 #2848

反応方程式

N-methyl piperidine

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

trichloroethyl chloroformate

→

title compound

収率 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

収率 75.0%

溶媒

CH2Cl2 DMF

EtOAc

反応条件

後処理

1. 1
   洗浄The organic layer is washed with 1N HCl, H2O, saturated NaCl
2. 2
   乾燥The organic layer is dried over MgSO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The residue is purified by column chromatography
6. 6
   洗浄eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

実験手順

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.

出典