FR_session_7_8 - H O + Br OEt O t-BuOK t-BuOH O O OEt This...

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Chem 3580 – Spring 2009 Friday Session 7 & 8 1. Provide the forward synthesis for each retrosynthetic analysis. O OH O O O OH O O O H O O O OEt O OH O OEt Warfarin (racemic) anticoagulant (blood thinner) + + (a) NH 2 COOH NH 2 COOEt CN COOH COOEt COOEt O COOEt COOEt Gabapentin (b) N O O Ph Phensuximide OEt OEt O O Ph OH OH O O Ph Ph H OEt O OEt O O NC OEt O Ph OEt O OH O Ph OH O OH O (c) 2. Provide a laboratory synthesis for the following compounds from the indicated starting materials O H H from EtO OEt O O Br Br (a) N CO 2 Me MeO 2 C H NO 2 from H O MeO OMe O O NH 3 Nifedipine (Procardia) (b) NO 2 NH 2 (c) N from OH OH O O and H 2 N (d) Taken from FR Session 5 Q2(f) N H (e)
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3. Suggest a plausible mechanism for each of the following reactions. H O H OH 1. CH 3 COO Na + 2. H 2 O, HCl O H O + O O O (a) ————————————————————————————————————
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Unformatted text preview: H O + Br OEt O t-BuOK t-BuOH O O OEt This is Darzens condensation reaction OEt OEt O O + O 1. NaOEt, EtOH 2. H 3 O + O O EtO 2 C CO 2 Et (b) Ph Ph O O I 2 (exs) HO PhCOO + HCI 3 (yellow precipitate) (c) Ph H O 1. EtO (1 equiv), EtOH 2. KCN, EtOH 3. H 3 O + , ! Ph CO 2 H CO 2 H + NC CO 2 Et (d) 4. Design synthesis for the compounds shown. N N H (b) N (a) N Ph (c) O + O Ph HONH 2 from +...
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FR_session_7_8 - H O + Br OEt O t-BuOK t-BuOH O O OEt This...

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