1,2-Dichloroethane → tert-Butyl 5-carbamoylisoindoline-2-carboxylate

Participants

Reaction Steps

A mixture of N-t-butoxycarbonyl-5-carboxyisoindoline (D13) (240 mg), EDC (350 mg), HOBT (140 mg), triethylamine (0.32 ml) and 0.880 ammonia solution (1 ml) in DMF (10 ml) was stirred overnight at rt and then evaporated. The residue was partitioned between EtOAc (10 ml) and 5% citric acid (10 ml). The organic layer was collected, washed with water (10 ml), saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and evaporated to give the title compound (D14) (154 mg). MS electrospray (+ion) 263 (MH+). 1H NMR δ (CDCl3), 7.73 (2H, m), 7.26 (1H, m), 6.88 (2H, m), 4.72 (2H, s), 4.69 (2H, s),1.52 (9H, s).

Provenance & Evidence