16.48 D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions. CHO D rosiglitazone H
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- 17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N TamoxifenQuinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).
- Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOH
- 18.31 Aldehydes that have no a hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when they are treated with concentrated base. An example is the following reaction of benzaldehyde: ororo H HO™ OH H₂O 2 + (a) When the reaction is carried out in D₂O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is CBH-CH₂OD. What does this suggest about the mechanism for the reaction? (b) When (CH3)2CHCHO and Ba(OH)₂/H₂O are heated in a sealed tube, the reaction produces only (CH3)₂CHCH₂OH and [(CH3)₂CHCO₂]2Ba. Provide an explanation for the formation of these products.D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.18.20 Write a stepwise mechanism for each of the following reactions. (a) O H (c) O HOG NaOH, H₂O -A NaOH, H₂O d of Plz solve all parts within 30-40 I'll upvote your answer (b) CH3 H NaOD D₂O you bou H D CH3 O Then sh
- Attenol A and pinnatoxin A are natural products isolated from marine sources. (a) Locate the acetals, hemiacetals, imines, and enamines in both compounds. (b) Draw the hydrolysis product formed when attenol A is treated with aqueous acid. Include stereochemistry at all stereogenic centers.Predict the products of reactions of ethers and epoxides, including the following:(a) Cleavage and autoxidation of ethers(b) Acid- and base-promoted opening of epoxides(c) Reactions of epoxides with organometallic reagents(d) Cleavage of silyl ethersRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, aniline