Triethylamine → HCID 86718995, compound

Participants

Reaction Conditions

Reaction Steps

To 4-nitrophenyl chloroformate (1084 mg, 5.38 mmol) in THF (18 mL) at 0° C. was added ethyl carbazate (560 mg, 5.38 mmol) and Et3N (2.98 mL, 21.52 mmol). The mixture was stirred at 0° C. for 1 h. Then more Et3N (2.98 mL, 21.52 mmol) was added, followed by a solution of 2,3-bis(prop-2-ynyloxy)propan-1-amine (I-13b: 5.92 mmol) in 5 mL THF, and the mixture was stirred at room temperature for 30 min. Water was added, extracted twice with AcOEt, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (40-100% AcOEt/heptane), giving ethyl 2-(2,3-bis(prop-2-ynyloxy)propylcarbamoyl)hydrazinecarboxylate (I-13c: 855 mg, 54%) as a light yellow oil. LC-MS (M+1) 298.2, t=0.75 minute.

Provenance & Evidence