Simple Preparation of N-Protected Chiral β-Amino Alkyl Thiols from Corresponding Iodides Employing Sodium Trithiocarbonate

A simple protocol for the preparation of N-protected amino alkyl thiols is reported that employs a reaction of sodium trithiocarbonate (Na2CS3) with N-protected amino alkyl iodides. Na2CS3 is easy to prepare and the protocol circumvents the use of strong bases and multiple steps. All the thiol compounds made were obtained as enantiopure samples and were characterized employing NMR and mass spectrometry

Synthesis of beta-lactam peptidomimetics through Ugi MCR: first application of chiral N-beta-Fmoc amino alkyl isonitriles in MCRs

Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved

Facile N-Urethane-Protected α-Amino/PeptideThioacid Preparation Using EDC and Na2S

We report herein an efficient protocol for the synthesis of N-urethane-protected α-amino/peptide thioacids from their corresponding acids mediated by EDC and Na2S. The fast reaction under mild conditions enabled the process to be completed in shorter duration with good yield circumventing column purification. The chemistry is compatible with a wide variety of urethane protecting groups, side-chain functionalities, and sterically hindered amino ­acids

ChemInform Abstract: A Simple Synthesis of Nβ‐Fmoc/Z‐Amino Alkyl Thiols and Their Use in the Synthesis of Nβ‐Fmoc/Z‐Amino Alkyl Sulfonic Acids

Starting from N-protected aminoalkyl iodides and thiourea, an efficient synthesis of the corresponding thiols proceeds via isothiouronium salts

An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator

A simple and efficient method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propane phosphonic acid cyclic anhydride (T3P) and subsequent reduction of the intermediate phosphonic anhydride with NaBH 4 yield the alcohol in excellent yields with good purity in less duration. Reduction of several alkyl/aryl carboxylic acids and N α-protected amino acids/peptide acids as well as N β-protected amino acids was successfully carried out to obtain corresponding alcohols in good yields and the products characterized. The procedure is mild, safe, simple and the isolation of the products is easy. © 2012 Elsevier Ltd. All rights reserved

Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU

The reaction of Nα-protected amino/peptide acid with N,O-dimethylhydroxylamine hydrochloride in the presence of T3P and DBU to obtain enantiomerically pure Nα-protected amino/peptidyl Weinreb amides in high yields has been described. Fmoc-Ala-Weinreb amide 2a is obtained as single crystal, and its structure was determined through X-ray crystallography. © 2012 Published by Elsevier Ltd

Chiral N β-Fmoc-amino alkyl isonitriles in Ugi-4CR: An assembly of novel 1,1â²-iminodicarboxylated peptidomimetics

Enantiopure N β-Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1â²-iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters. © 2011 Elsevier Ltd. All rights reserved

Synthesis of chiral Nβ-protected amino diselenides from the corresponding amino alkyl iodides using NaBH2Se3 as a selenating reagent and their conversion to seleninic acids

A convenient approach has been presented for the synthesis of Nβ-protected amino diselenides from the corresponding amino alkyl iodides using in situ generated NaBH2Se3 as an efficient selenating reagent. All the diselenides are obtained in good yields under very mild conditions, short duration times and the protocol is free from racemization. The methodology has been effectively extended to the synthesis of N-protected L-selenocystine methyl ester. Clean oxidation of Nβ-protected amino diselenides to Nβ-protected amino seleninic acids using 35% aqueous H2O2 has also been accomplished. The present protocol is compatible with all the common urethane protecting groups. Graphical abstract: Synthesis of chiral Nβ-protected amino diselenides from the corresponding amino alkyl iodides using NaBH2Se3 as a selenating reagent and their conversion to seleninic acid

ChemInform Abstract: One‐Pot Synthesis of Ureido Peptides and Urea‐Tethered Glycosylated Amino Acids Employing Deoxo‐Fluor and TMSN3

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