Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: Br₂ 0 (1) -Br 1-bromoadamantane Adamantane CH,—CHBr AlBr3 (2) Br -Br
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- A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2Chlorophyll, heme, vitamin B12, and a host of other substances are synthesized from porphobilinogen, which is itself formed from the condensation of two molecules of 5-aminolevulinate. The two 5-aminolevulinates are bound to lysine (Lys) residues in the enzyme, one in the enamine form and the other in the imine form. Condensation is thought to occur via a several step process, one of which is shown below. ÇO2 ÇO2 CO2 + NH3 NH3 H H3N 5-aminolevulinate (enamine form) 5-aminolevulinate (imine form) Porphobilinogen Draw curved arrows to illustrate the movement of electrons in this step of the reaction. Arrow-pushing Instructions CO2 CO2 CO2 CO2 :B BH* H-A H3N H3ŅRimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: CH₂=CHBr AlBr3 (2) Adamantane =D₂.-6. (3) -Br Br (4) Ø Br₂ (1) a Step 2 proceeds via the following mechanism: 1-bromoadamantane (5) Br SnF ChemDoodle Rimantadine 1. AlBr, acts as a Lewis acid to yield carbocation 1; 2. Bromoethene acts as a nucleophile to give carbocation 2; 3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2. Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3. NH₂ ==starting points == ✔
- Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of the neurotransmitter serotonin in the synapses of the central nervous system follow- ing release of serotonin during excitation of individual nerve cells. Between firings, the serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of reuptake has the effect of increasing the time serotonin molecules remain in the syn- apses following excitation, leading to a therapeutic effect. In one synthesis of parox- etine, the following reagents are used. Draw the structures of synthetic intermediates A and B. F НО SOCI, A B HO PyridineCompound D, shown below, reacts with hydrogen bromide by electrophilic addition. A mixture of two organic compounds, E and F, is formed. CH3 CH₂CH₂ CH3 H compound D HBr Mixture of organic compounds E and F (i) Name the the two organic compounds E and F and show their condensed formula. (ii) Briefly explain the mechanism of the reaction between compound D and hydrogen bromide to form either compound E or compound F. (You can list/state the main steps) (iii) Which compound, E or F is the major product?The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
- 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?Draw the structure of the product/s in each of the following reactions. Ethanoyl chloride(A) Acetic Anhydride NANO2, HCI, H,O, 0ºC Propanamine (B) + (C) OH- H,0 (D) (E)(c) Consider the antiallergy medication loratadine (Claritin) shown below: Loratadine (Claritin) The reaction to form the portion of the molecule in the red circle is used in the synthesis of loratadine and many other pharmaceutical agents. (i) Propose a suitable starting material and reagents to form the portion of the molecule in the red circle. (ii) Clearly outline the mechanism by which the reaction takes place. In your answer, show how the intermediate ion is stabilized.
- When the enzymatic decarboxylation of acetoacetate is carried out in H218O, all the acetone that is formed contains 18O. What does this tell you about the mechanism of the reaction?How are the following conversions carried out? (i) Aniline to nitrobenzene (ii) Ethanamine to N-ethylethanamide (iii) Chloroethane to propan-1-aminePredict the products formed when limonene reacts with the followingreagents.(a) excess HBr (b) excess HBr, peroxides (c) excess Br2 in CCl4(d) ozone, followed by dimethyl sulfide