4-Methylmorpholine → HCID 131723142, compound

Participants

Reaction Conditions

Reaction Steps

To 5 g (0.014 mol) of Z-Ala-Ala-AlaOH dissolved in THF/DMF 1:1 (50 mL) at −10° C. under a N2 atmosphere were added 1.6 mL (0.014 mol) NMM and 1.9 mL (0.014 mol) IBCF. The reaction mixture was stirred 15 minutes, filtered, and the filtrate added slowly to an ice-cold solution of NaBH4 (1.4 g, 0.037 mol) in H2O (3 mL) and stirred 1 hour at ice-bath temperature and 1 hour at room temperature. The reaction mixture was cooled to 0° C. and treated with saturated NaHCO3 solution, extracted with EtOAc, washed with 1M HCl that is saturated with NaHCO3, dried over anhydrous MgSO4, and evaporated to dryness. The crude product was purified over a silica gel column eluted with 95:5 EtOAc/MeOH to give 1.2 g product.

Provenance & Evidence