Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question
What is the percentage yield and write the reaction for this experiment .
product weight =4.55g
![EXPERIMENT 2: Synthesis of a potential enzyme inhibitor
AIM
To undertake the synthesis of an enzyme inhibitor as a potential anti-tumour agent in the
treatment of hormone-dependent breast cancer.
INTRODUCTION:
The enzyme estrone sulfatase (ES) is responsible for the conversion of stored estrogens
(sulfated) to the active (non-sulfated) estrogens (Figure 1).
HO-
-0
но-
6
Figure 1. The reaction catalysed by the enzyme estrone sulfatase
ES
Inhibitors of this enzyme have shown to be useful in the fight against hormone-dependent breast
cancer. In this experiment, you will synthesise a potential inhibitor of this enzyme i.e.:
HC-fa
CH₁₂
HO
15
H₂C
0
CH₂
METHOD
Methane sulfonyl chloride is extremely lachrymatory as well as being sensitive to moisture and
corrosive! The WHOLE of this practical MUST be carried out using a fume hood - no part of it
is to be carried out in the general laboratory. Do not use naked flames AND do not walk
around the laboratory with open top flasks.
Add 3g of 4-hydroxyacetophenone to 70ml anhydrous dichloromethane in a 250cm³ round
bottom flask. Then add 5ml of triethylamine and stir the mixture for a 1 minute. Cool the
mixture to 0°C in an ice bath and add 3ml of methane sulfonyl chloride whilst stirring the solution
by hand using a glass rod. Add 2-4 anti-bumping granules. Using a heating mantle, reflux the
reaction mixture for 45 minutes. After cooling to room temperature, carefully pour the reaction
mixture into a beaker containing approximately 100cm³ of ice. After the ice has melted, wash
the dichloromethane layer twice with water (50ml each time). Wash the dichloromethane twice
with saturated sodium bicarbonate (NaHCO3) solution (50ml each time) and finally once with
water (80ml). Dry the dichloromethane layer over anhydrous magnesium sulfate. After filtering
off the solid magnesium sulfate, remove the dichloromethane using a rotary evaporator. You
should avoid smelling the product as there may still be some residue of methane sulfonyl
chloride present in the round bottom flask. Record the weight and therefore determine the
percentage yield.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F41b14d1f-73f2-4dc7-941e-5aa0f83a3c41%2F3cc07dfa-9b35-40ec-a57d-d6d1ca6e1b1d%2F82mlchr_processed.png&w=3840&q=75)
Transcribed Image Text:EXPERIMENT 2: Synthesis of a potential enzyme inhibitor
AIM
To undertake the synthesis of an enzyme inhibitor as a potential anti-tumour agent in the
treatment of hormone-dependent breast cancer.
INTRODUCTION:
The enzyme estrone sulfatase (ES) is responsible for the conversion of stored estrogens
(sulfated) to the active (non-sulfated) estrogens (Figure 1).
HO-
-0
но-
6
Figure 1. The reaction catalysed by the enzyme estrone sulfatase
ES
Inhibitors of this enzyme have shown to be useful in the fight against hormone-dependent breast
cancer. In this experiment, you will synthesise a potential inhibitor of this enzyme i.e.:
HC-fa
CH₁₂
HO
15
H₂C
0
CH₂
METHOD
Methane sulfonyl chloride is extremely lachrymatory as well as being sensitive to moisture and
corrosive! The WHOLE of this practical MUST be carried out using a fume hood - no part of it
is to be carried out in the general laboratory. Do not use naked flames AND do not walk
around the laboratory with open top flasks.
Add 3g of 4-hydroxyacetophenone to 70ml anhydrous dichloromethane in a 250cm³ round
bottom flask. Then add 5ml of triethylamine and stir the mixture for a 1 minute. Cool the
mixture to 0°C in an ice bath and add 3ml of methane sulfonyl chloride whilst stirring the solution
by hand using a glass rod. Add 2-4 anti-bumping granules. Using a heating mantle, reflux the
reaction mixture for 45 minutes. After cooling to room temperature, carefully pour the reaction
mixture into a beaker containing approximately 100cm³ of ice. After the ice has melted, wash
the dichloromethane layer twice with water (50ml each time). Wash the dichloromethane twice
with saturated sodium bicarbonate (NaHCO3) solution (50ml each time) and finally once with
water (80ml). Dry the dichloromethane layer over anhydrous magnesium sulfate. After filtering
off the solid magnesium sulfate, remove the dichloromethane using a rotary evaporator. You
should avoid smelling the product as there may still be some residue of methane sulfonyl
chloride present in the round bottom flask. Record the weight and therefore determine the
percentage yield.
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