Hydrochloric Acid → Methyl 3-(2-{2-[2-(2-(methylamino)ethoxy)ethoxy]ethoxy}ethoxy)propanoate

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Reaction Steps

3 ml of a 4M solution of HCl in dioxane are added to 390 mg of methyl 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate in solution in 5.3 ml of dioxane. After 12 h at AT, the mixture is concentrated under RP and the residue is dissolved in a minimum of methanol and deposited on Mega BE-SCX, 10GM 60ML (Varian). After washing the phase with MeOH, the product of interest is eluted with a 2N solution of ammonia in methanol. The methanol/NH3 phase is concentrated under RP. 270 mg of methyl 3-(2-{2-[2-(2-(methylamino)ethoxy)ethoxy]ethoxy}ethoxy)propanoate are thus obtained. 1H NMR (400 MHz, d5-DMSO): 2.28 (s, 3H); 2.54 (t, J=6.2 Hz, 2H); 2.59 (t, J=5.9 Hz, 2H); 3.44 (t, J=5.9 Hz, 2H); 3.47 to 3.54 (m, 12H); 3.60 (s, 3H); 3.63 (t, J=6.2 Hz, 2H). LC/MS (A) (ELSD): rt=0.30 min; [M+H]+: m/z 294.

Provenance & Evidence