McGriff, Richard Bernard (1959) The synthesis of 1-keto-3-carbomethoxy-1,2,3,4-tetrahydroisequinoline. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechTHESIS:05102010-153156629
The preparation of 1-keto-3-carbomethoxy-1,2,3,4-tetrahydroisequinoline byt wo routes is described. The first involves hydrolysis of the adduct of a-bromo-o-tolunitrile and acetamidomalinicester to 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline. Esterification of this acid yields the desired ester. The second route involves the condensation of phenylalanine with formaldehyde to form 3-carboxy-1,2,3,4-tetrahydroisequinoline. The benzoyle derivative of this compounds is smoothly oxidized by cold permanganate to N-benzoyl (o-carboxyphenyl) alanine, wich is convert by acid hydrolysis to 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline and benzoic acid. Preliminary experiments show that 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline is hydrolyzed by a-chymotrypsin, and indicate that both forms are hydrolyzed,albeit at differing rates.
|Item Type:||Thesis (Master's thesis)|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||1 January 1959|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Tony Diaz|
|Deposited On:||18 Aug 2010 18:42|
|Last Modified:||26 Dec 2012 03:25|
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