Ethyl 1-trityl-1H-imidazole-4-carboxylate

Synthesis

To a stirred solution of ethyl imidazole-4-carboxylate (2 g; 14 mmol) in dimethylformamide (50 ml) at 0 °C were sequentially added triphenylchloromethane (3.98 g; 14 mmol) and triethylamine (1.73 g, 17 mmol). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was cooled, concentrated under reduced pressure and subsequently diluted with water. The aqueous layer was extracted with ethyl acetate and the organic layers were combined. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give ethyl 1-trityl-1H-imidazole-4-carboxylate (XLV) as a brown solid (3 g, 55% yield). Mass spectrometry analysis showed a molecular ion peak (M + 1) of 383.34.

References

[1] Farmaco, Edizione Scientifica, 1985, vol. 40, # 8, p. 541 - 554
[2] Patent: WO2015/97122, 2015, A1. Location in patent: Page/Page column 96; 97
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256
[4] Patent: US4935437, 1990, A
[5] Patent: US2016/272594, 2016, A1. Location in patent: Paragraph 0023