In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease Inhibitors, published in 2001-08-01, which mentions a compound: 138775-03-8, Name is (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, Molecular C18H24N2O6, Formula: C18H24N2O6.
Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogs of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asym. alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to trans-nitroalkene Ph-CH2-CH:CH-NO2, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asym. synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones (I; F, CH2Ph trans and I; F, CH2Ph = cis; diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (II; Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochem. is discussed.
After consulting a lot of data, we found that this compound(138775-03-8)Formula: C18H24N2O6 can be used in many types of reactions. And in most cases, this compound has more advantages.
Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com