Organic Chemistry of Drug Synthesis. Volume 7

HO OCNSO 2 Cl SO

O 2

H 2 O

HCl

CH 2 Cl KCN CN OH– CO 2 H

OCN SO

O 2

H 2 N

SO

O 2

HN

118 119 120 121

122 123 124

125

O

CH 2 =O

The pH of intracellular space is known to fall during ischemic episodes,
heart surgery, and other events that compromise cardiac function. This
encourages entry of sodium and calcium into cardiac cells. The resulting
calcium overload may then compromise contractile function. The recently
developed antiarrhythmic agentcariporide( 130 ) has been found to act by
specifically inhibiting the sodium–proton exchange that leads to further
injury. Chlorosulfonation ofp-isopropylbenzoic acid leads to the chloro-
sulfonyl derivative ( 127 ). Treatment of intermediate 127 with sodium
sulfite in base serves to reduce the newly introduced function to the

CO 2 H

126

ClSO CO^2 H

3 H

ClO 2 S

127

Na 2 SO 3 HO^2 S CO^2 H

128

CH 3 Br

NaOH

H OS^2 CO^2 H

1. SO 2 Cl 3 C


2. H 2 N NH
   NH 2

OS 2

H 3 C NH

O

NH 2

NH

130 129

4. COMPOUNDS RELATED TO ARYLSULFONIC ACIDS 57