17360-47-3Relevant articles and documents
Solid phase reductive alkylation of secondary amines
Khan, Nawaz M.,Arumugam, Vijayalakshmi,Balasubramanian, Shankar
, p. 4819 - 4822 (1996)
Solid phase reductive alkylation of secondary amines has been carried out in excellent yields using borane-pyridine complex (BAP). Various aldehydes and ketones have been reacted with L-proline substituted on high-capacity Wang Resin.
N-ALKYLATED AMINO ACIDS AND OLIGOPEPTIDES, USES THEREOF AND METHODS FOR PROVIDING THEM.
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Page/Page column 17-19; 26; 28-31; 45, (2018/10/25)
The invention relates to the synthesis of amphiphilic amino acid derivatives, in particular to a method for the N-alkylation of an unprotected amino acid or the N-terminus of an oligopeptide substrate, comprising reacting said unprotected amino acid or oligopeptide substrate with an alcohol, e.g. a fatty alcohol, in the presence of a homogeneous transition metal catalyst.
SN1-type substitution reactions of N-protected β-hydroxytyrosine esters: Stereoselective synthesis of β-Aryl and β-alkyltyrosines
Wilcke, David,Herdtweck, Eberhardt,Bach, Thorsten
supporting information; experimental part, p. 1372 - 1382 (2012/07/30)
The title compounds were prepared by aldol reaction of anisaldehyde and the respective N,N-dibenzyl glycinates. Deprotection of the nitrogen atom with Pearlman's catalyst delivered the unprotected β-hydroxytyrosine esters, which were further N-protected as N,N-phthaloyl (Phth) and N- fluorenylmethylcarbonyloxy (Fmoc) derivatives. The Friedel-Crafts reaction with various arenes was studied employing these alcohols as electrophiles. It turned out that the facial diastereoselectivitiy depends on the nitrogen protecting group and on the ester group. The unprotected substrates (NH2) gave preferentially syn-products but the anti-selectivity increased when going from NHFmoc over NPhth to NBn2. If the ester substituent was varied the syn-preference increased in the order Me A model is suggested to explain the facial diastereoselectivity based on a conformationally locked benzylic cation intermediate. The reactions are preparatively useful for the N-unprotected isopropyl ester, which gave Friedel-Crafts alkylation products with good syn-selectivity (anti/syn=21:79 to 7:93), and for the N,N-dibenzyl-protected methyl ester, which led preferentially to anti-products (anti/syn=80:20 to >95:5). Upon acetylation of the latter compound to the respective acetate, Bi(OTf)3-catalyzed alkylation reactions became possible, in which silyl enol ethers served as nucleophiles. The respective alkylation products were obtained in high yield and with excellent anti-selectivitiy (anti/syn≥95:5). Copyright
Analogues of arginine vasopressin (AVP) modified in the N-terminal part of the molecule with N-benzylglycine
Jastrzebska,Derdowska,Kuncarowa,Slaninova,Lammek,Olejniczak,Zabrocki
, p. 823 - 830 (2007/10/03)
The synthesis and some pharmacological properties of five new analogues of arginine vasopressin (AVP) substituted with N-benzylglycine are described. All new peptides were tested for pressor and uterotonic activity. The results obtained imply that the structural change studied is in general incompatible with interaction of the analogues with V1A and OT receptors, however, in combination with suitable additional changes, may be of value in the design of new antagonists of these receptors.
Scope and limitation of the acid-catalyzed isomerization of Aib-containing thiopeptides
Breitenmoser, Roland A.,Heimgartner, Heinz
, p. 786 - 796 (2007/10/03)
The use of amino thio S-acids in the 'azirine/oxazolone method' and a novel isomerization led to Aib-containing endothiopeptides. With the aim of generalizing this method, a variety of Aib-containing dipeptide thioanilides have been prepared. By their treatment with ZnCl2 in AcOH, followed by HCl-saturated AcOH, the C=S group was shifted from the last to the penultimate amino acid in high yield and without epimerization. As this methodology is very useful for the specific introduction of a thioamide group, it was extended to Aib-containing tripeptides. In addition, it could be shown that a mechanism via spirocyclic intermediates (cf. Scheme 4) is most likely for this isomerization. To establish the proposed neighboring-group participation of the N-acyl group, model dipeptide thioanilides containing no N-terminal C=O group were synthesized. These derivatives did not undergo rearrangement.
Fast ester cleavage of sterically hindered α- and β-aminoesters under non-aqueous conditions. Application to the kinetic resolution of aziridine esters
Alezra, Valérie,Bouchet, Céline,Micouin, Laurent,Bonin, Martine,Husson, Henri-Philippe
, p. 655 - 658 (2007/10/03)
Various protected α- and β-aminoesters undergo fast ester cleavage by treatment with t-BuOK in THF. The accelerating effect of a neighboring chelating group was used for the efficient kinetic resolution of non-racemic aziridine esters. (C) 2000 elsevier Science Ltd.
