Succinic anhydride → 3-(Bis(((t-butyloxy)carbonyl)methyl)carbamoyl)propanoic acid

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Reaction Steps

Compound 14 (0.88 g, 3.59 mmol), succinic anhydride (0.377 g, 3.77 mmol), ethyldiisopropylamine (625 μL, 3.59 mmol) and 4-di(methylamino)pyridine (44 mg, 0.359 mmol) were dissolved in CHCl3 (15 mL) and stirred for 48 h. The mixture was diluted with dichloromethane (140 mL) and the organic layer was washed with H2O (2×75 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80% EtOAc in hexanes) to give the compound 15 (0.9 g, 72.6%). 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.47 (s, 9H), 2.62 (t, J=5.8, 2H), 2.69 (t, J=5.8, 2H), 4.02 (s, 2H), 4.06 (s, 2H). ESI-MS calculated for C16H27NO7, 345.59 found 368.1 (M+Na).

Provenance & Evidence