Triethylamine → HCID 86640101, compound

Participants

Reaction Steps

(Z)-8-(2-morpholinoethylamino)-7-((naphthalen-1-yloxy)methyl)oct-6-enoic acid (268 mg, 0.63 mmol) obtained in Example (3-1-2) was dissolved in N,N′-dimethylformal (3.2 ml) in a 25 ml vessel, and to the resulting mixture, N-hydroxy-6-trifluorobenzotriazole (FOBt; 140 mg, 0.69 mmol, 1.1 eq.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl; 157 mg, 0.82 mmol, 1.3 eq.), tetrahydro-2H-pyran-2-yloxyamine (THPONH2; 111 mg, 0.95 mmol, 1.5 eq.), and triethylamine (0.18 ml, 1.26 mmol, 1.5 eq.) were added at 0° C., while stirring. The resulting mixture was heated to room temperature and stirred for 12 hrs. After the completion of reaction, 10% aqueous potassium carbonate solution was added to the reaction mixture, and then the resultant was extracted with ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 142 mg of the title compound as dark yellow foam (yield 43%).

Provenance & Evidence