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 (5.1 g, 0.02 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSCDI), (3.83 g, 0.02 mol). Approximately 20 mL of CH2Cl2 was used to wash the reagents into the reaction flask. After the mixture was stirred over night the solvent was evaporated off and the residue was treated with ethyl acetate: HCl. 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. The titled product (3.4g) was collected as a colorless oil (Rf: 0.7,silica gel, CH2Cl2 : CH3OH 97:3 ) and used it as is for saponification.

Provenance & Evidence