tert-Butyl carbazate → HCID 68697521, compound

Participants

Reaction Steps

To a solution of 1-(3-chloro-4-cyano-2-methylphenyl)proline (0.623 g, 2.350 mmol), N,N-diisopropylethylamine (1.420 g, 11.750 mmol) and TBTU (1.113 g, 3.530 mmol) in DMF add a solution of t-butlycarbazate (0.462 g, 3.530 mmols) in DMF. Leave to stand for 3 h, then partition between ethyl acetate and 10% (w/w) aqueous citric acid. Extract the organic with 2N aqueous sodium hydroxide solution, then brine. Dry over magnesium sulphate, filter, and concentrate under reduced pressure to obtain the title compound. (0.89 g, 100%) mass spectrum (m/e): 379 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.80 (s, 1H), 7.42 (d, 1H), 6.38 (d, 1H), 6.22 (bs, 1H) 4.33 (t, 1H), 3.88 (m, 1H), 3.04 (m, 1H), 2.81 (m, 3H), 2.53 (m, 1H), 1.85-2.38 (m. 3H), 1.41 (s, 9H).

Provenance & Evidence