Reaction #1904052

Reaction equation

dimethyl (S)-{2-amino-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}phosphonate

4-chlorophenyl isocyanate

→

(S)-2-[3-(4-chlorophenyl)ureido]-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)propionamide

Yield 100.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe methylene chloride solution is subsequently washed successively with 10 ml of each of 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and water
2. 2
   Dryingdried over sodium sulfate
3. 3
   workup.ADDITION10 ml of diethyl ether are added to the residue
4. 4
   Filtrationthe white precipitate deposited is filtered off

Procedure

5.4 The solution of 0.2 g (0.54 mmol) of dimethyl (S)-{2-amino-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}phosphonate and 0.092 g (0.54 mmol) of 4-chlorophenyl isocyanate in 10 ml of dichloromethane is stirred at room temperature for 12 hours. The methylene chloride solution is subsequently washed successively with 10 ml of each of 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and water and dried over sodium sulfate. After the solvent has been stripped off, 10 ml of diethyl ether are added to the residue, and the white precipitate deposited is filtered off, giving 0.28 g (100%) of (S)-2-[3-(4-chlorophenyl)ureido]-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)propionamide (“1D”), ESI 525.

Source