Methanol → HCID 54556555, compound

Participants

Reaction Steps

To a solution of 6.4 g succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate in 40 ml of ethanol at ? 0° C. is added in one portion a solution of 1.008 g of the above D-serylglycine in 10 ml of water at 70° C. The reaction mixture is refluxed for i hour and then stirred at room temperature overnight. After evaporation of the solvents the residue is agitated with 25 ml of acetone. The precipitate is removed by filtration. Diethylether is added to the filtrate until precipitation is complete. The precipitate is collected by filtration and washed with diethylether. After drying 1.56 g of a yellowish powder is obtained. To 600 mg of this is added 15 ml of chilled methanol. After agitation during 5 min. the white precipitate is filtered off, washed with cold methanol and dried to obtain 400 mg of S-benzoylmercaptoacetylglycyl-D-serylglycine as a white powder, m.p. 149° C. N.M.R. (DMSO-d6):δ3.61 (2H, d, CH2 --OH), 3.77 (2H, d, α--CH2 --N), 3.84 (2H, d,β--CH2 --N), 3.88 (2H, s, S--CH2), 4.38 (1H, dr, CH), 8.03 (1H, d,β--NH), 8.17 (1H, t,α--NH), 8.44 (1H, t,γ--NH).

Provenance & Evidence