Dimethylformamide → Carbamic acid, (3-amino-2-methyl-3-oxopropyl)-, 1,1-dimethylethyl ester

Participants

Reaction Steps

BOC-β-alanine (0.50 g, 2.64 mmol) was dissolved in 4 mL DMF. Methylamine hydrochloride (198 mg, 2.93 mmol) and DMAP (427.2 mg, 3.50 mmol) were added, followed by EDCI (1.06 g, 5.53 mmol). After stirring at room temperature for 2 days the solvent was removed in a stream of nitrogen and the residue dried in vacuo. It was dissolved in 5 mL 1 M HCl, and the solution was extracted five times with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to yield 0.43 g (2.13 mmol, 81%) of BOC-β-alanine methylamide (14) as a white solid. mp. 117-118° C., 1H-NMR (300 MHz, CDCl3) δ 5.78 (b, NH), 5.15 (b, NH), 3.38 (q, J=6.1 Hz, 2H), 2.78 (d, J=4.8 Hz, 3H), 2.36 (t, J=6.1 Hz, 2H), 1.40 (s, 9H) 13C-NMR (75.5 MHz, CDCl3) δ 171.74 (C), 79.15 (C), 36.41 (CH2), 36.03 (CH2), 28.17 (3 CH3), 26.04 (CH3).

Provenance & Evidence