12 Starting with only propene, synthesize the following amino acid. The listed compound is your only allowable sources of carbon other than any inorganic nitrile (must contain a metal)! All other inorganic reagents are allowable. You MUST go through 3-oxobutanenitrile as an intermediate in this synthesis! OH HO NH2 CH3
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- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the…Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.
- In the Gabriel synthesis of primary amines, N-potassiophthalimide is used as a source of the nitrogen atom. Complete the synthesis reactions by drawing the missing structures. Ignore inorganic counterions. NH2 N K* DMF Step 1 Product NaOH (xs) H2O, heat Step 2 Product Br KBrNOC XT Ph CH₂ Both primary and secondary amines add to a ß-unsaturated aldehydes and ketones to yield ß-amino aldehydes and ketones rather than the alternative imines. Under typical reaction conditions, both direct and conjugate modes of addition occur rapidly. But because the reactions are reversible, they generally proceed with thermodynamic control rather than kinetic control so the more stable conjugate addition product is often obtained to the complete exclusion of the less stable direct addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H H CH3NH₂ CH3 H-A :A Ph NHCH3 вон CH3 :A H-A 8bShow how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
- 27) Hydrolysis of an ester: O II CH,-C-O-CH2-CH2-CH, + H20 28) Acid/ Base reaction of an amine CH3-CH2-NH2 H2CO3 29) Hydrolysis of an amide 11 CH3-CH2-CH2-CH2-CH2-C-NH-CH2-CH2-CH, + H20 OMIC MoleculesStarting with cyclohexanone and ethanol as the only organic reagents, use any inorganic reagents to propose a synthesis for the target molecule.Propose a retrosynthetic analysis of benzocaine from the starting material shown. Your answer should include both the synthons and the reagents that would be employed in the actual synthesis. H2N
- There are three steps in Somfai's short synthesis of the alkaloid, stemoamide. Supply the missing reagents and products in this three-reaction sequence in the middle of the synthesis. H. 1) I-B: BRZNCH2CO2ET Grubbs-II P Q R CH2CI2 (Ph3P)4Pd THF-DMPU, A 2) НОАС C11H16|NO C15H23NO3 C13H19NO34. Here’s a figure-it-out mechanism, resulting in the formation of p-aminophenol from an aromatic hydroxylamine. Would you expect either ortho- or meta-aminophenol to form in competition? Why or why not? H H;0* H -N НО H2O ОН H 5. (a) The triaryl hydroxylamine hydrolyzes in acid to form two products: one compound containing two aromatic rings and one with a single aromatic ring. First, draw the two products and the mechanism of their formation in acidic water (this is another "figure it out" mechanism). Ph H;O* Ph—С—N H,0 Ph ОН (b) Suppose one of the aryl rings had a t-donating group (-OCH3) and the other had a n- withdrawing group (-NO2), both in the para position. Where would the substituents end up in the products (draw them)? Why? Do you suspect this reaction is under kinetic control or thermodynamic control, or both/either?b) Show a complete reaction mechanism for the synthesis of compound K via malonic ester synthesis. Show all the reagents and draw the intermediate structures. COOH Compound K