Answered: NH Na+ 'N' 'N' + EtO 'N' H H H Sodium…

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter31: Immunochemistry

Section: Chapter Questions

Problem 31.75P

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Question

Several sulfonylureas, a class of compounds containing RSO₂NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.

NH Na+
'N'
'N'
+ EtO
'N'
H
H H
Sodium salt of
A carbamic ester
Tolbutamide
p-toluenesulfonamide
(Orinase)

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