FR_session_9_correction_to_Q1 - Aspartame O Phenylalanine...

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Chem 3580 – Spring 2009 Friday Session 9 – Correction to Q1 1. Propose a reasonable synthesis for the sweetener Aspartame from the indicated starting compounds. The error is in the phenylalanine structure, one of the starting amino acids. There is an extra carbon. The extra carbon has been removed. The error has no impart on the synthesis. H 3 N N H H O CO 2 H H Ph O OCH 3 N O O CO 2 Et CO 2 Et Br H 3 N OCH 3 H Ph from and
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Unformatted text preview: Aspartame O Phenylalanine 1. Answer H N N H O H Ph O OCH 3 N O O CO 2 Et CO 2 Et Br H 2 N H Ph 1. EtO , EtOH 2. N O O CO 2 Et CO 2 Et 1. HO , H 2 O, ! 2. H 3 O + , ! H 3 N CO 2 H Hydrolysis, decarboxylation 1. neutralize 2. Protect amine BOC 2 O H N COO O t-Bu DCC 1. O 3 2. H 2 O 2 3. CF 3 CO 2 H H 3 N N H O H Ph O OCH 3 CO 2 H O t-Bu O O O OCH 3...
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This note was uploaded on 10/25/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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