Home >
Community >
Selective secondary amide/lactam hydrolysis
Upvote
VOTE
Downvote
+ Chemistry
+ Synthesis
Posted by
Kamal L C
Selective secondary amide/lactam hydrolysis
Drawing on the comments of @user55119 above, I am going to to summarise the comments as an answer.
There is no way of selectively hydrolysing the acetanilide in the presence of the lactam.
It doesn't matter because the lactam can be readily reformed from the completely hydrolysed material by treatment with a carbodiimide such as 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The free phenol and aniline are unlikely to interfere as they are less nucleophilic than the secondary amine and you are forming a [5] ring with the lactam.
Drawing on the comments of @user55119 above, I am going to to summarise the comments as an answer.
There is no way of selectively hydrolysing the acetanilide in the presence of the lactam.
It doesn't matter because the lactam can be readily reformed from the completely hydrolysed material by treatment with a carbodiimide such as 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The free phenol and aniline are unlikely to interfere as they are less nucleophilic than the secondary amine and you are forming a [5] ring with the lactam.
Drawing on the comments of @user55119 above, I am going to to summarise the comments as an answer.
There is no way of selectively hydrolysing the acetanilide in the presence of the lactam.
It doesn't matter because the lactam can be readily reformed from the completely hydrolysed material by treatment with a carbodiimide such as 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The free phenol and aniline are unlikely to interfere as they are less nucleophilic than the secondary amine and you are forming a [5] ring with the lactam.
Drawing on the comments of @user55119 above, I am going to to summarise the comments as an answer.
There is no way of selectively hydrolysing the acetanilide in the presence of the lactam.
It doesn't matter because the lactam can be readily reformed from the completely hydrolysed material by treatment with a carbodiimide such as 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The free phenol and aniline are unlikely to interfere as they are less nucleophilic than the secondary amine and you are forming a [5] ring with the lactam.
More
VOTE