Undecylenic Acid → 3-(Undec-10-enoylamino)-dihydropyridine-2,6(1h,2h)-dione

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

(S)-3-(tert-Butoxycarbonylamino)glutarimide (a compound of formula XV wherein R1 is tert-butoxy; R2 is hydrogen, R3 and R4 together with the atoms to which they are attached are a six membered heterocyclic ring comprising five carbon atoms and N(H); R5 is hydrogen; and the center marked by * has the (S) configuration; 228 mg, 1 mmol) was dissolved in CH2Cl2 (2 mL) and the solution was cooled to 0° C. Trifluoroacetic acid (1 mL) was added dropwise, and the reaction was stirred for 1 hour. The reaction was then reduced in vacuo to give crude (S)-glutarimidyl-3-ammonium trifluoroacetate as a thick oil. This material was dissolved in DMF (1.5 mL) and (i-Pr)2NEt (1.5 mL), and the resulting solution was added to a solution of 10-undecenoic acid (1 mmol) and BOP (442 mg, 1 mmol) in DMF at 25° C. This reaction was stirred for 24 hours, and was then partitioned between EtOAc (30 mL) and 0.5 M HCl(aq) (20 mL). The organic layer was then washed twice more with 0.5 M HCl(aq) (20 mL), dried over Na2SO4 and reduced in vacuo to give a white solid which was chromatographed (SiO2/EtOAc) to give the title compound.

Herkunft & Nachweise