1,2-Dichloroethane → Boc-Ala-Gly-Gly-OBzl

Participants

Reaction Conditions

Reaction Steps

One equivalent of 0.39 g (2 mmol) EDC (Aldrich) is added into a stirred solution of 0.5 g (2 mmol) of Boc Ala-Gly-OH (12), 0.4 g of (2 mmol) of Gly-OBzl (Sigma), 0.27 g of HOBT (Aldrich), and 0.2 ml of NMM in 100 ml of DCM at ice bath temperature. The reaction mixture is stirred for 3 h at 0° C. and 22 h at ambient temperature. The reaction mixture is concentrated using a rotary evaporator, and the residue is dissolved in 100 ml of ethyl acetate. The ethyl acetate solution is extracted with 10% NaHCO3 and water. The organic layer is dried over anhydrous Na2SO4 and isolated by decantation. Then, the ethyl acetate is evaporated to furnish the Boc-Ala-Gly-Gly-OBzl (13) as a yellow oil which is confirmed by MS and NMR. 1H-NMR (CDCl3): 1.28 (3H, d, J=7.2 Hz), 1.31 (9H, s), 3.85-4.15 (5H, m), 5.06 (2H, s), 5.45 (1H, br), 7.25 (5H, br), 7.41 (1H, br). FABMS: 394 (M+1).

Provenance & Evidence