1,2-Dichloroethane → Ammonium Hydroxide

Participants

Reaction Steps

(±)-tert-Butyl[2-(aminocarbonyl)-5-nitro-2,3-dihydro-1H-inden-2-yl]carbamate A solution of (±)-2-[(tent-butoxycarbonyl)amino]-5-nitroindane-2-carboxylic acid from Step C (470 mg, 1.46 mmol), ammonium chloride (156 mg, 2.92 mmol), EDC (419 mg, 2.19 mmol), HORT (335 mg, 2.19 mmol), and DIEA (1.27 mL, 7.29 mmol) in DMF (5 mL) was stirred at ambient temperature for 16 h. The reaction mixture was poured onto saturated NaHCO3 (20 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:9:1, to give the title compound. MS: m/z=322 (M+1).

Provenance & Evidence