N-Carbobenzoxy-L-valine → HCID 18649007, compound

Participants

Reaction Steps

To a solution of CBZ-L-valine (5.0 g, 0.02 mol)in CH2Cl2 (50 mL) were added 4-dimethylaminopyridine (2.44 g, 0.02 mol), N-(2-indanyl)glycine ethyl ester hydrochloride (5.6 g, 0.02 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSCDI) (3.83 g, 0.02 mol). Approximately 20 mL CH2Cl2 was used to wash the reagents into the reaction flask. After the mixture was stirred overnight the solvent was removed under vacuo and the residue treated with ethyl acetate: 1N HCl (3:1). The separated organic layer was washed with 1N HCl, 5% aqueous Na2CO3 and saturated aqueous NaCl-solution followed by drying over magnesium sulfate and filtration. After removal of the solvent under reduced pressure an oil (4.3 g) remained, which was purified over silica gel using CH2Cl2 as eluent. 3.4 g of a colorless oil was collected (Rf: 0.7, silica gel, CH2Cl2 :CH2OH 97:3 ) and used as is for saponification.

Provenance & Evidence