Triethylamine → HCID 18646450, compound

Participants

Reaction Steps

A solution of N-benzyloxycarbonyl-L-leucine (2.65 g, 10 mmol) in 15 ml CH2Cl2 was cooled in an ice-water bath and stirred with a magnetic stirrer. A solution of dicyclohexylcarbodiimide (2.58 g, 12.5 mmol) in CH2Cl2 was added, and stirring was continued for 15 minutes. Dicyclohexylurea was filtered. The solvent was evaporated in vacuo or at room temperature. The residue was dissolved in 4 ml DMF(1) and cooled in an ice-water bath. CF3CO2H·H-Val-Gly-OMe(1.51 g, 5 mmol) was dissolved in 7 ml DMF, and Et3N (0.25 g =0.34 ml, 2.5 mmol) was added, whereupon the mixture was added to the solution (1) and Et3N (0.34 ml) was again added. Stirring was continued for 24 hours at room temperature. The reaction mixture was filtered, diluted with water and AcOEt and separated. The water layer was extracted twice with AcOEt. Collected organic phases were washed once with water, once with 0.5M NaHCO3, once with water, once with 1N HCl, and twice with water and dried over anhydrous MgSO4. After filtration the solvent was evaporated in vacuo. The solid residue was triturated with petroleum ether, filtered and dried in vacuo.

Provenance & Evidence