Reaction #82331

Reaction equation

[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl bromide

N2 L-prolyl-N1 -isobutyl-L-isoleucinamide

triethylamine

→

N2 [N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-prolyl]-N1 -isobutyl-L-isoleucinamide

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe solvent was removed by evaporation
2. 2
   Otherthe crude product was chromatographed on silica gel
3. 3
   Washfor the elution
4. 4
   OtherThe resulting product was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and ethyl acetate

Procedure

A solution of 8.86 g of [N-(benzyloxycarbonyl)-L-phenylalanyl]methyl bromide 6.71 g of N2 -L-prolyl-N1 -isobutyl-L-isoleucinamide and 2.60 g of triethylamine in 400 ml of dichloromethane was stirred at room temperature overnight. The solvent was removed by evaporation and the crude product was chromatographed on silica gel using ethyl acetate for the elution. The resulting product was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and ethyl acetate to give 8.70 g of N2 -[N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-prolyl]-N1 -isobutyl-L-isoleucinamide as an off-white solid of m.p. 80°-81° C.

Source