Reaction #2842

Reaction equation

triethylamine

3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride

benzo[b]thiophene-2-sulfonyl chloride

→

title compound

Yield 79.0%

Benzo[b]thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Yield 79.0%

Solvents

EtOAc

CH2Cl2

Conditions

Workup

1. 1
   WashThe solution is washed with 1N HCl, saturated NaHCO3, and saturated NaCl
2. 2
   DryingThe organic layer is dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Procedure

To a solution of 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride (0.36 g, 1.43 mmol) in 15 mL of CH2Cl2 is added benzo[b]thiophene-2-sulfonyl chloride (0.32 g, 1.38 mmol). To the resulting solution is added triethylamine (0.29 g, 2.88 mmol). After 16 h, the solution is diluted with EtOAc. The solution is washed with 1N HCl, saturated NaHCO3, and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The title compound (0.45 g, 1.09 mmol) is obtained as white solid.

Source