hex-5-enoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Methyl-N-{[methyl(hex-5-enyl)amino]carbonyl}-L-valine was prepared according to the procedure for 3-methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valine (Steps 1-5) by using 5-hexenoyl chloride instead of 4-pentenoyl chloride in Step 1. LRMS (ESI) m/z 271 [(M+H)+; calcd for C14H27N2O3: 271].

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 6-methoxy-[1,5]naphthyridin-4-ylamine (1.5 g, 8.56 mmol) and TEA (1.55 mL, 1.3 eq.) in DCM (8.5 mL) was added 5-hexenoyl chloride (1.36 g, 1.2 eq.) in DCM (1.5 mL) at rt. The resulting suspension was vigorously stirred at rt for 20 h. The mixture was then washed with water. The org. layer was dried over Na2SO4 and concentrated. The residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4) to afford the title intermediate as a yellow solid (1.66 g, 71% yield). The mixture was then washed with water layer was dried over Na2SO4 concentrated The residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Methyl-N-{[methyl(hex-5-enyl)amino]carbonyl}-L-valine was prepared according to the procedure for 3-methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valine (Steps 1-5) by using 5-hexenoyl chloride instead of 4-pentenoyl chloride in Step 1. LRMS (ESI) m/z 271 [(M+H)+; calcd for C14H27N2O3: 271].