112924-08-0Relevant articles and documents
TERT-BUTYL ESTERS OF N-PROTECTED AMINO ACIDS WITH TERT-BUTYL FLUOROCARBONATE (Boc-F)
Loffet, A.,Galeotti, N.,Jouin, P.,Castro, B.
, p. 6859 - 6860 (1989)
Tert-butyl fluorocarbonate (Boc-F) is efficiently used for the synthesis of tert-butyl esters of N-protected amino acids.The reaction proceeds at room temperature and under mild conditions in the presence of triethylamine and 4-dimethylamino-pyridine.
Facile synthesis of tert-butyl ester of N-protected amino acids with tert-butyl bromide
Chevallet, Pierre,Garrouste, Patrick,Malawska, Barbara,Martinez, Jean
, p. 7409 - 7412 (1993)
A facile synthesis of a wide variety of N-benzyloxycarbonyl-amino acid-tert-butyl ester derivatives under mild conditions is described. N-protected amino acids were esterified with tert-butyl bromide in dimethylacetamide as solvent, in the presence of benzyltriethylammonium chloride (BTEAC)and a large excess of potassium carbonate. Many amino Z-acid-Tert-butyl esters that might be difficult to prepare by other methods have been synthesized in high yields by this procedure. The reaction is simple, unexpansive, easily scaled up, and proceeds without observable racemization.
Convenient and Simple Esterification in Continuous-Flow Systems using g-DMAP
Okuno, Yoshinori,Isomura, Shigeki,Sugamata, Anna,Tamahori, Kaoru,Fukuhara, Ami,Kashiwagi, Miyu,Kitagawa, Yuuichi,Kasai, Emiri,Takeda, Kazuyoshi
, p. 3587 - 3589 (2015/11/17)
The utility and applicability of polyethylene-g-polyacrylic acid-immobilized dimethylaminopyridine (g-DMAP) as a catalyst in a continuous-flow system were investigated for decarboxylative esterification. High catalytic activity toward acylation was provided by g-DMAP containing a flexible grafted-polymer structure. During decarboxylation, carboxylic acids and alcohols were converted cleanly using di-tert-butyl dicarbonate (Boc2O) as a coupling reagent, which reduced by-products. In addition, the use of Boc2O resulted in the formation of tert-butyl esters. These esterifications dramatically reduced the reaction time under continuous-flow conditions, with a residence time of approximately 2 min. This highly efficient esterification procedure will provide more practical industrial applications.
Toward the selective delivery of chemotherapeutics into tumor cells by targeting peptide transporters: Tailored gold-based anticancer peptidomimetics
Negom Kouodom, Morelle,Ronconi, Luca,Celegato, Marta,Nardon, Chiara,Marchiò, Luciano,Dou, Q. Ping,Aldinucci, Donatella,Formaggio, Fernando,Fregona, Dolores
supporting information; scheme or table, p. 2212 - 2226 (2012/05/05)
Complexes [AuIIIX2(dtc-Sar-AA-O(t-Bu))] (AA = Gly, X = Br (1)/Cl (2); AA = Aib, X = Br (3)/Cl (4); AA = l-Phe, X = Br (5)/Cl (6)) were designed on purpose in order to obtain gold(III)-based anticancer peptidomimetics that might specifically target two peptide transporters (namely, PEPT1 and PEPT2) upregulated in several tumor cells. All the compounds were characterized by means of FT-IR and mono- and multidimensional NMR spectroscopy, and the crystal structure of [AuIIIBr2(dtc-Sar-Aib-O(t- Bu))] (3) was solved and refined. According to in vitro cytotoxicity studies, the Aib-containing complexes 3 and 4 turned out to be the most effective toward all the human tumor cell lines evaluated (PC3, DU145, 2008, C13, and L540), reporting IC50 values much lower than that of cisplatin. Remarkably, they showed no cross-resistance with cisplatin itself and were proved to inhibit tumor cell proliferation by inducing either apoptosis or late apoptosis/necrosis depending on the cell lines. Biological results are here reported and discussed in terms of the structure-activity relationship.
