Question

Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?

Short answer

Temozolomide is a cancer-fighting drug that can be taken orally. When its present in the circulatory system, it is transformed into its active form by combining with water and losing carbon dioxide.

When it is present inside the cell, it eliminates a methyl diazonium ion.

Step-by-step solution

Temozolomide

Temozolomide is a cancer-fighting drug that can be taken orally. When its present in the circulatory system, it is transformed into its active form by combining with water and losing carbon dioxide.

When it is present inside the cell, it eliminates a methyl diazonium ion.

Identifying the amide bond that is hydrolyzed in the first step of the conversion of temozolomide to methyl diazonium

The carbon dioxide molecule is lost immediately after the hydrolysis of the amide bond. The bond indicated below is the amide bond that is hydrolyzed, as carbon dioxide can be lost since the electrons left behind can be delocalized onto the carbonyl oxygen.