Friday_session_9_sol - Chem 3580 Spring 2009 Friday Session 9 Solution These problems contain a lot of practice mechanisms for quite a number of

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Chem 3580 – Spring 2009 Friday Session 9 - Solution These problems contain a lot of practice mechanisms for quite a number of reactions. Go through and practice them. Pay attention to how protecting groups are used in a couple of cases. 1. H N N H O H Ph O OCH 3 N O O CO 2 Et CO 2 Et Br H 2 N OCH 3 O 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 2. N H O O H (a) Br OTHP N O O H 3 N H 3 O + , ! N O O CO 2 Et CO 2 Et CO 2 Et CO 2 Et 1. EtO (1 equiv) 2. COOH OTHP OH HBr H 2 N COOH Br ! (excess) S N 2 displacement of Br by NH 2 hydrolysis of all groups including THP followed by decarboxylation H 3 N O OH O (b) N O O CO 2 Et CO 2 Et 1. EtO (1 equiv) 2. H O 3. H 3 O + work-up N O O CO 2 Et CO 2 Et OH 1. H 3 O + , ! 2. neutralize hydrolysis decarboxylation
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CH 3 CONH CO 2 Et CO 2 Et 1. EtO (1 equiv) 2. EtO 2 C (CH 2 ) 4 OSiMe 3 CH 3 CONH CO 2 Et Br(CH 2 ) 4 OSiMe 3 F EtO 2 C (CH 2 ) 4 OH CH 3 CONH CO 2 Et PCC EtO 2 C (CH 2 ) 3 CHO CH 3 CONH CO 2 Et 1. NH 3 , NaBH 3 CN, AcOH 2. H 3 O + , ! H 3 N O NH 2 O Protect OH to be removed under non-acidic conditions removal of SiMe 3 group oxidation of OH to aldehyde Reductive amination followed by acid
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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Friday_session_9_sol - Chem 3580 Spring 2009 Friday Session 9 Solution These problems contain a lot of practice mechanisms for quite a number of

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