130608-07-0Relevant articles and documents
Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles
Vidal, Joelle,Guy, Laure,Sterin, Sebastien,Collet, Andre
, p. 4791 - 4793 (1993)
We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).
SULFONAMIDE COMPOUNDS HAVING TNAP INHIBITORY ACTIVITY
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Page/Page column 112; 153; 154; 155, (2018/07/29)
The present invention relates to a compound or a pharmacologically acceptable salt thereof having excellent tissue non-specific alkaline phosphatase inhibitory activity. The present invention provides a compound represented by the formula (I) or a pharmacologically acceptable salt thereof.
Access to Enantiopure α-Hydrazino Acids for N-Amino Peptide Synthesis
Kang, Chang Won,Sarnowski, Matthew P.,Elbatrawi, Yassin M.,Del Valle, Juan R.
, p. 1833 - 1841 (2017/02/10)
Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydrazino acids derived from 19 out of the 20 canonical proteinogenic amino acids and demonstrate their use in the solid-phase synthesis of N-amino peptide derivatives.
Low-cost and multi-gram scale synthesis of chiral Nβ-Boc protected α-Nα-hydrazino diesters
Mehawed Abdellatif, Mohamed,Acherar, Samir
supporting information, p. 1216 - 1218 (2017/03/02)
An efficient and general low-cost method is described to obtain chiral Nβ-Boc protected α-Nα-hydrazino diester building-blocks (orthogonally and non-orthogonally protected diesters) on multi-gram scale (30?mmol) using two successive
Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides
Kang, Chang Won,Ranatunga, Sujeewa,Sarnowski, Matthew P.,Del Valle, Juan R.
supporting information, p. 5434 - 5437 (2015/02/19)
The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues. (Chemical Equation Presented).
N-amination of amino acids and its derivatives using N-Boc-O-tosyl hydroxylamine as an efficient NH-Boc transfer reagent: Electrophilic amination
Baburaj, Thankappan,Thambidurai, Sivalingam
experimental part, p. 2292 - 2294 (2012/07/17)
Terminal tert-butyloxycarbonyl (Boc) protected hydrazino acids, useful intermediates for modified peptides and biologically active heterocyclic derivatives, were synthesized by electrophilic amination methodology using N-Boc-O-tosyl hydroxylamine as an ef
Catalytic enantioselective hydrogenation of N-alkoxycarbonyl hydrazones: A practical synthesis of chiral hydrazines
Yoshikawap, Naoki,Tan, Lushi,Christopher McWilliams,Ramasamy, Deepa,Sheppard, Ruth
supporting information; experimental part, p. 276 - 279 (2010/03/25)
(Figure presented) An enantioselective hydrogenation of hydrazones catalyzed by Rh complexes (Rh-Josiphos or Rh-Taniaphos) has been developed. The protocol can be applied to hydrazones with three different protective groups (Boc, Cbz, and methoxycarbonyl)
N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents
Vidal, Joelle,Damestoy, Stephanie,Guy, Laure,Hannachi, Jean-Christophe,Aubry, Andre,Collet, Andre
, p. 1691 - 1709 (2007/10/03)
This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
THE PREPARATION OF 2-HYDRAZINYL ESTERS IN HIGH OPTICAL PURITY FROM 2-SULFONYLOXY ESTERS
Hoffmann, Robert V.,Kim, Hwa-Ok
, p. 2953 - 2956 (2007/10/02)
Chiral 2-triflyloxy esters, prepared from chiral 2-hydroxy esters, react enantiospecifically with BocNHNH2 to produce optically pure 2-hydrazinyl ester derivatives in high yields.The reaction of 2-nosyloxy esters with BocNHNH2 gives 2-(Boc-hydrazinyl) esters, thus providing an efficient (albeit slow) method for the conversion of esters to 2-hydrazinyl ester derivatives.
