Reaction #952

Reaction equation

benzyl chloroformate

( ii )

4-amidino benzyl azide

triethyl amine

HCl

Benzyl chloroformate

→

4-(benzyloxycarbonylamidino) benzyl azide

Solvents

water

methylene chloride

Conditions

Workup

1. 1
   Dryingthe resulting solution was dried (K2CO3)
2. 2
   Filtrationfiltered
3. 3
   Temperaturewas cooled in an ice bath
4. 4
   DryingThe organic phase was dried (MgSO4)
5. 5
   Otherthe solvent was removed in vacuo

Procedure

The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an additional 2 ml benzyl chloroformate was added and stirring was continued for another 30 minutes. Subsequently, water was added and the aqueous phase was adjusted to pH 7 with 2M HCl. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. 4-(benzyloxycarbonylamidino) benzyl azide was finally isolated as colorless crystals from ether/methylene chloride/hexane.

Source