Cyanoacetamide → Carboxyamidotriazole

Participants

Reaction Steps

After protection of the alcohol group in 3,5-dichlorobenzyl alcohol, as the TBDMS ether step (step 1), the ether is reacted with 4 chlorobenzoyl chloride to form the substituted benzophene (step 2). The benzophene is treated with thionyl chloride (step 3) and then with sodium azide (step 4) to form 3,5-dichloro-4-(4-chlorobenzoyl)benzyl azide. Reaction of this azide with cyanoacetamide produces L651582 (step 5). Reaction of L651582 with orotic acid forms the L651582 orotate (2:1) (step 6).

Provenance & Evidence