4-Methylmorpholine → HCID 86740025, compound

Participants

Reaction Steps

Tertiarybutoxycarbonyl-L-norleucine (13.2 g) in CH2Cl2 (200 ml) was treated at 0° with L-alanine N-butylamide (5.25 g), DCC (7.77 g) and 1-hydroxybenzotriazole (5 g). The pH of the reaction mixture was adjusted to 7 with N-methyl morpholine and allowed to warm to room temperature overnight. The precipitated urea was filtered off and the filtrate washed successively with saturated aqueous sodium hydrogen carbonate, water and 1M citric acid. The organic phase was dried over sodium sulphate and the solvent evaporated in vacuo. The residue was chromatographed on silica in a gradient of 30-70% ethyl acetate in dichloromethane. Elution with 50% ethyl acetate in dichloromethane afforded the title compound (7.6 g) which crystallised from ethyl acetate as needles m.p. 108°-112°; (Found: C,60.8; H,9.8; N,11.8. C18H35N3O4 requires C,60.5; H,9.9; N,11.75%); νmax (Nujol) 3280, 3340 1675 and 1640 cms-1 δ (CDCl3) 0.9 and 0.91 (each 3H, each t, each J=5 Hz, 2×CH3); 1.1-1.9 (10H, m, (CH2)3 and (CH2)2); 1.38 (3H, d, J=5 Hz, 6H2CHCH3); 1.44 (9H, s, C(CH3)3); 3.24 (2H, tt, J=5 Hz NHCH2) and 4.1 and 4.48 (each 1H, each m, 2×CH).

Provenance & Evidence