Methyl bromoacetate → (S)-methyl 2-(3-(tert-butoxycarbonylamino)-2-oxoazepan-1-yl)acetate

Participants

Reaction Steps

To a round bottom flask was added (S)-tert-butyl 2-oxoazepan-3-ylcarbamate (130 mg, 0.569 mmol), THF (10 mL) and LiHMDS (0.190 mL, 1.14 mmol). The reaction was stirred at rt for 30 min. Then methyl 2-bromoacetate (0.079 mL, 0.85 mmol) was added to the reaction and the reaction mixture was stirred at rt overnight. The reaction mixture was concentrated and purified by RP prep-HPLC to give (S)-methyl 2-(3-(tert-butoxycarbonylamino)-2-oxoazepan-1-yl)acetate (60 mg, 0.20 mmol, 35% yield) as a clear oil. Anal. Calcd. for C14H24N2O5 m/z 300.3. found: 301.2 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 5.89 (br. s., 1H), 4.40 (d, J=4.4 Hz, 1H), 4.13 (br. s., 2H), 3.79-3.56 (m, 4H), 3.15 (d, J=12.1 Hz, 1H), 2.07-1.87 (m, 2H), 1.75 (d, J=10.4 Hz, 2H), 1.62-1.49 (m, 2H), 1.39 (br. s., 9H); 13C NMR (126 MHz, CDCl3) δ ppm 173.82, 169.55, 155.20, 79.55, 53.36, 52.17, 50.71, 50.63, 32.21, 28.31, 27.80, 26.87.

Provenance & Evidence