Synthesis of Ibuprofen
It acts on compounds called prostaglandins:
Physiologically active lipid compounds having diverse hormone
Found in almost every tissue in human
They are derived enzymatically from fatty acids
They bring out inflammatory response
Ibuprofen's action as a painkiller and fever-reducing compound
is due to its ability to inhibit the synthesis of prostaglandins
It does this by interfering with the action of an enzyme
called cyclooxygenase which catalyzes the conversion of a
compound called arachidonic acid into prostaglandins
4 step Ibuprofen synthesis
First step:
Nucleophilic addition Reduction of the carbonyl
group C=O by sodium tetrahydridoborate produces
a secondary alcohol group CHOH.
Second step: Sn1 nucleophilic substitution of the
hydroxyl group
To improve reactivity of alcohols the leaving anion
OH is converted into H2O
CH3)3COH + HCl (37%) (CH3)3COH2(+) Cl()
(CH3)3C(+) Cl() + H2O (CH3)3CCl + H2O (SN1 )
Third step:
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