4-Methylmorpholine → HCID 131726470, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 239 mg (0.419 mmol) Aloc-D-Ala-Trp-Lys(Aloc)-OH 28 was dissolved in dry tetrahydrofuran under an argon atmosphere and cooled to −40° C. N-methylmorpholine (48.3 μl, 1.05 equiv) and isobutylchloroformate (57.0 μl, 1.05 equiv) were added. The reaction mixture was stirred for 2 hours at a temperature below −30° C. A solution of 4-aminobenzyl alcohol (51.5 mg, 1.00 equiv) and N-methylmorpholine (50.6 μl, 1.1 equiv) in dry THF was added dropwise to the reaction mixture. After 2 hours tetrahydrofuran was evaporated and dichloromethane was added. The organic layer was washed with saturated sodium bicarbonate, a 0.5 N potassium bisulphate solution and brine, dried (Na2SO4) and evaporated to afford 265 mg (94%) of the desired product 29 as a cream coloured powder. 1H-NMR (300 MHz, CDCl3/CD3OD): δ 1.00–1.62 (m, 9H, CH3-Ala and 3 CH2-Lys), 2.90–3.70 (m, 4H, N—CH2-Lys and CH2-Trp), 4.48–4.92 (m, 7H, 2 Hα and 4 Aloc), 4.72 (s, 2H, CH2—OH), 5.00–5.50 (m, 5H, 4 Aloc and Hα), 5.35–6.05 (m, 2H, Aloc), 6.80–7.83 (m, 9H, aromatic) ppm; MS (FAB) m/e 677 (M+H)+, 699 (M+Na)+.

Provenance & Evidence