Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

Nα-Glycyl-Nε-carbobenzoxy-L-lysine (10.1 g.) prepared by the method of Rao et al. (J. Biol. Chem., 198,507 1952) was dissolved in methanol (150 ml.) and treated with boron trifluoride etherate (30 ml.) and the mixture heated at 80°C for 25 hours. The solvent was removed in vacuo and the residual oil dissolved in water (100 ml.) and extracted with ether (2 × 50 ml.) and the extracts discarded. The aqueous solution was adjusted to pH 9.0 with 4N sodium hydroxide, saturated with sodium chloride and extracted with ethyl acetate (3 × 50 ml.). The combined extracts were washed with saturated brine, dried (MgSO4) and the solvent removed in vacuo to give a residual oil which was redissolved in ethanol (10 ml.) and treated with an excess of an ethereal solution of hydrogen chloride. The solid was filtered and recrystallised from isopropanol/diisopropyl ether to give Nα-glycyl-Nε-carbobenzoxy-L-lysine methyl ester hydrochloride, needles (4.5 g.) m.p. 122°C. (Found: C, 53.0; H, 6.8; N, 10.8. C17H25N3O5. HCl requires: C, 52.6; H, 6.7; N, 10.8%).

Provenance & Evidence