N-(2,4-Dinitrophenyl)glycine → HCID 86609788, compound

Participants

Reaction Steps

To a stirred solution of 3 (0.25 g, 0.42 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.1 g, 0.5 mmol) in dichloromethane (50 mL) was added N-(2,4-dinitrophenyl)glycine (0.11 g, 0.51 mmol), and the solution was left to react at room temperature overnight. The solution was washed with 0.01 M HCl (1×100 mL), 0.2 M NaOH (1×100 mL), and brine solution (1×100 mL). The solution was dried (MgSO4) and evaporated to dryness. The crude compound was chromatographed (SiO2/EtOAc→MeOH) to yield 0.26 g (0.33 mmol, 79%) of 6 as a yellow oil. 1H NMR (CDCl3, 500 MHz): δ1.12-1.42 (br m, 14H), 1.57-1.62 (br m, 2H), 1.63-1.72 (br t, 2H), 2.12-2.21 (br m, 2H), 3.41-3.61 (br m, 12H), 4.17-4.21 (d, 2H), 5.87-5.92 (br s, 1H), 6.89-6.94 (d, 1H), 7.14-7.24 (m, 6H), 7.31-7.39 (m, 9H), 8.26-8.32 (d, 1H), 9.14-9.21 (br d, 1H). C44H55N5O8S (813.38): m/z 812.7 [M−H+]−.

Provenance & Evidence