Reaction #1178450

Reaction equation

4-nitrophenyl chloroformate

pyridine

4-(4-aminophenyl)morpholin-3-one

(R)-2-(4-chlorophenylcarbamoyl)pyrrolidinium chloride

N-ethyldiisopropylamine

→

2-N-[(4-chlorophenyl)]-1-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-pyrrolidine-1,2-dicarboxamide

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 12 hours
2. 2
   Otherevaporated
3. 3
   Otherthe residue is chromatographed on a silica-gel column

Procedure

1.01 g (5.00 mmol) of 4-nitrophenyl chloroformate and 0.404 ml (5.00 mmol) of pyridine are added to a solution of 961 mg (5.00 mmol) of 4-(4-aminophenyl)morpholin-3-one in 10 ml of dichloromethane, and the mixture is stirred at room temperature for 1 hour. 1.31 g (5.00 mmol) of (R)-2-(4-chlorophenylcarbamoyl)pyrrolidinium chloride and 2.55 ml (15.0 mmol) of N-ethyldiisopropylamine are added to the suspension. The reaction mixture is stirred at room temperature for 12 hours and then evaporated, and the residue is chromatographed on a silica-gel column, giving 2-N-[(4-chlorophenyl)]-1-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(R)-pyrrolidine-1,2-dicarboxamide as a yellowish solid, ESI 443.

Source