Diethyl azodicarboxylate → HCID 23317256, compound

Participants

Reaction Steps

The Cbz protected serylaminomalonate (0.5 g, 1.2 mmoles) and 0.33 g (1.2 mmoles) of TPP in 30 mL of THF were treated with 0.2 mL (1.29 mmoles) of DEAD for 1 hour at R.T. The mixture was chromatographed as above, yielding 0.29 g (63% mass recovery) of the mixture of the title compound and 1-Cbz-2-carboxyaziridine diethoxycarbonylmethylamide. 105 mg of the mixture was prep TLC'd (silica, 2 mm, ether/hexanes, 4 times). The title compound eluted first, and after evaporation, 64.1 mg (0.18 mmoles, 15%) was isolated as an oil. IR (neat) 1770, 1750, 1715. NMR 1.13-1.33 (6H, m), 3.56-3.7 (2H, m), 4.0-4.4 (4H, m), 4.6-4.8 (1H, m), 5.1 (3H, 2 overlapping singlets), 5.8-6 (1H, m), 7.4 (5H, s). The aziridine side product: 39.5 mg (0.1 mmoles, 8.7%) IR (neat) 1760, 1730. NMR 1.16-1.33 (6H, t), 2.4-2.6 (2H, dd), 3.06-3.16 (1H, dd), 4.1-4.4 (4H, dq), 4.5-4.8 (1H, b), 5.06-5.1 (1H, d), 5.13 (2H, s), 7.4 (5H, s).

Provenance & Evidence