Trifluoroacetic acid → Methyl 2-{[2-(morpholin-4-yl)ethyl]amino}acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5](C(OC(C)(C)C)=O)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1Participants
4
Procedure
A solution of [tert-butoxycarbonyl-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester (0.79 g, 2.61 mmol) in CH2Cl2 (10 mL) was treated with TFA (10 mL). After stirring at room temperature for 1 h, the solution was concentrated in vacuo. The oil was dissolved in CH2Cl2 (50 mL) and the resulting solution was washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (10×50 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (0.40 g, 76%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 3.69-3.74 (m, 7H), 3.45 (s, 2H), 2.69-2.73 (m, 2H), 2.45-2.52 (m, 6H), 1.84 (s, 1H).