Hydrochloric Acid → Methyl 3-(2-{2-[2-(2-(methylamino)ethoxy)ethoxy]ethoxy}ethoxy)propanoate
Reaction equation
Cl.C(O[C:7]([N:9](C)[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=O)(C)(C)C>O1CCOCC1>[CH3:7][NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- concentrationthe mixture is concentrated under RP
- dissolutionthe residue is dissolved in a minimum of methanol
- washAfter washing the phase with MeOH
- washthe product of interest is eluted with a 2N solution of ammonia in methanol
- concentrationThe methanol/NH3 phase is concentrated under RP
Sources & evidence
- ORD record
- ord-6e083e6a660a4a81852b8a63291ac02a
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481042B2
Reaction notes
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