CH203 Fall 2014 Lecture 9 September 22

8/11/2019 CH203 Fall 2014 Lecture 9 September 22

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(S)-Naproxen

100% - ee = % of the sample which is a racemic mixture

100% - 97% = 3% is a racemic mixture

!x 3% = 1.5% = the amount of S in the racemic mixture

Total %S = 97% + 1.5% = 98.5%

Total %R = 1.5%


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(")-(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol


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l02/O&0/I; -,O#02;

Anandamide,from the Sanskrit ananda,bliss

Identified 1992

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R C OO H B R C O O

H B

(R,R)-Salt + (S,R)-Salt)(R)-Base(R+ S)-Carboxylic

acid

:


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N N

(S)-1-Phenylethanamine (R)-1-Phenylethanamine

H

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HOO

H

OH

HO

O

OH

OH

OH

HO

O

O

OH

(2S,3S)-(+)-Tartaric acid (S)-(-)-Malic acid (1S,3R)-(+)-Camphoric acid


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f&;/-I%/0 /M n#02&-,$ S$,2Resolution ofMandelic Acid


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EtO O

NaOH H

2

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2. HCl H

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H

3

CO

CH

3

O OH

Ethyl ester of (S)-naproxen Ethyl ester of (R)-naproxen(not affected by the esterase)

+

1. esterase

(S)-Naproxen


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N

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side chain

Ionized or zwitterion

form of an amino acid

Zwitterion: a molecule containing a positive and a negative electrical charge which is

overall neutral. Sometimes called inner salts.


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Documents

CH203 Fall 2014 Lecture 9 September 22