4-Methylmorpholine → HCID 131711195, compound

Participants

Reaction Conditions

Reaction Steps

Boc-Asn-Ala-OBzl (XXIII) (27.54 g, 70 mmol) was treated with 4 N HCl/THF (875 ml) for 30 minutes at room temperature. Evaporation and treatment with dry ether provided 23.08 g (100%). The hydrochloride salt was dissolved in DMF (250 ml), cooled to 0° C and NMM (4.9 ml, 70 mmol) was added under stirring followed by Boc-Lys(Z)-OPfp (39.5 g, 72.3 mmol). The mixture was stirred for 1 hr at 0° C and 3 hr at room temperature. After evaporation of the solvent to a smaller volume, 0.5 N HCl was added and the precipitated product was collected by filtration and washed on the funnel with H2O, (5%) NaHCO3 and H2O. After drying, it was triturated with EtOAc and then with petroleum ether, yield 41.5 g (90.4%); mp 148°-150° C; [α]D25 -15.3° (c 2, DMF). Anal. Calcd for C33H45N5O9 (655.76): C, 60.44; H, 6.92; N, 10.68. Found: C, 60.50; H, 6.97; N, 10.70.

Provenance & Evidence