Fundamentals of Medicinal Chemistry

(Brent) #1
entered the brain, it is easily oxidized to the quaternary salt, which because of its
charge cannot return across the blood–brain barrier.

Chapter 10


(1) (i), (ii) See Section 10.2. (iii) See section 10.1.


(2) See Section 10.2.


(3) See Section 10.2.3.


(4) See Figure 10.10. Use propyliodide instead of ethyliodide in Figure 10.10.


(5) Synthon, see Section 10.3.1.


(i)


(ii)


(iii)


O

O

CH 3 CH 3 CH 3

Ph Ph −O Ph

−O

−O

+ O +

HO

HO

O
OC OC

OH
HOOC

+

+

COOC 2 H 5

COOC 2 H (^5) COOC
2 H 5 COOC 2 H 5
Cl Cl COOC 2 H (^5) Cl COOC 2 H 5
OH OH












  • C
    O
    H H
    2 C
    (iv) A pericyclic disconnection. O +
    CO
    CO
    O
    CO
    CO
    (6) FGI, see section 10.3.1.
    (i)
    HO
    HO HO HO
    NH COCH 3 HO
    HO
    NH

    NH 2
    NH 2




  • CH 3 COCl
    or
    (CH 3 CO) 2 O
    Reduction Nitration
    +COCH
    3
    FGI
    NO 2 + NO 2
    270 ANSWERS TO QUESTIONS



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