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- Propose a synthesis of the topical anesthetic cyclomethycaine from 4-hydroxybenzoic acid, 2-methylpiperidine, and any other necessary reagents. HN' + HO. НО Cyclomethycaine 4-Hydroxybenzoic acid 2-MethylpiperidineAlthough codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only one OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine. но. CH,0. [1 кон H [2] CH3I H. CH3 H Ho morphine H. CH3 Ho codeineProvide the mechanism for this reaction (include arrow pushing) ОН 2-lodobenzoic acid K2S2O8 H2SO4 ОН OSO3H ОН 양 diphenyliodonium-2-Carboxylate benzyne
- Following are two possible retrosynthetic analyses for the anticholinergic drug cycri- mine. Fill in the details of each potential synthesis. O: OH + H. Cycrimine (гасemic)Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nico- tinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide. COH COET CNH, Nicotinic acid Ethyl nicotinate Nicotinamide (Niacin)3) Venlafaxine is a Wyeth antidepressant that is synthesized on a commercial scale from the starting material shown. Suggest a plausible synthesis using the same starting material. MeO MeO H₂N. OH
- Give the major product for the reaction. Pyrrolidine is a secondary amine. CH CH O CH CH! O OH CH2 O CH. I CH.CH Ї TCH CHE OH CH CH₂CH₂ CH.CH CH.OH2 0= RO pyrrolidine. 2 GH CH2 3 HCI H,0 TOH OH: CH₂CH₂ TCH CH: CH₂CH. CH₂CH₂Following is an outline of a synthesis of the bronchodilator carbuterol, a beta-2 adrenergic blocker with high selectivity for airway smooth muscle receptors. Q.Why is it necessary to add the benzyl group, PhCH2—, as a blocking group in Step 1?18. The following drug (structure shown below) is a chemotherapy medication for the treatment of pleural mesothelioma and non-small cell lung cancer (NSCLC) in the clinic. CO2H HN- H2N- a) What's the target of this anticancer drug? Briefly describe its mechanism of action.
- 51. Which is NOT a valid resonance structure for the conjugate base of this molecule? (A) (C) S (A) OEt O :O: : OEt HBr ROOR OCH 3 (B) 52. What is the major product of this reaction sequence? O PPh3 (D) 11 Mg ether (B) de OEt :0 aom Сосно LOCH 3 53. Which reagent is necessary for this transformation? (D) H OEt H OEt CH31 PPh3 ACS 56.Draw a plausible mechanism for the formation of phenol shown below. Provide explanations for each step in the mechanism. (HINT: The mechanism involves electrocyclic reactions, NOT sigmatropic rearrangements.) HOʻa. What is the amine and coupling components of this azodye? H;CO- -N=N-
