Page 209 - Medicinal Chemistry Self Assessment

Replacement Structures for Batch 3
Chapter 2.20
Please replace the structure for answer 6B (page 5) with the one shown below.

Note: Aromaric hydroxylation
could also occur on these
rings; however, they are
more sterically hindered.

198 Medicinal Chemistry Self Assessment
Please replace the structure for answer 6C (page 6) with the one shown below.

C. Hydrolysis: Phase I; Yes

H CO O CH 3
3
O
OH
N S
H H
H O N O
Please replace the structure for answer 6D (page 6) with the one shown below.
O Note: It is also possible to
N hydrolyze the sulfonamide.
CH
3
Please replace the structure for answer 6D (page 6) with the one shown below.
O
D. Oxidative O-Dealkylation: Phase I; Yes CH
O
H H H O O 3
O N S Oxidative O-dealkylation
H H of methoxy functional group
O N H H H O O O CH 3
O
O N N S Oxidative O-dealkylation
H H of methoxy functional group
O N CH 3 O

O N

CH 3
O
H CO O CH 3
3
O
N S Oxidative O-dealkylation
O H H
H O N H CO O O CH 3 of carbamate functional group
3
O
O N N S Oxidative O-dealkylation
H H of carbamate functional group
H O N CH O
3

O
N
CH 3
Please replace the structure for answer 6E (page 6) with the one shown below.

E. Benzylic Oxidation: Phase I; Yes
Please replace the structure for answer 6E (page 6) with the one shown below.

Benzylic oxidation can occur at two sites;
however, the one in the middle of the
molecule is more sterically hindered.

Benzylic oxidation can occur at two sites;
however, the one in the middle of the
molecule is more sterically hindered.