146232-51-1

Usage

Uses

Used in Medicinal Chemistry:
(3R)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid is used as a building block for the synthesis of more complex compounds in medicinal chemistry. Its protected functional groups allow for selective reactions and the creation of diverse pharmaceutical agents.
Used in Organic Synthesis:
In organic synthesis, (3R)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid is used as a versatile intermediate. The t-butoxycarbonyl groups can be removed under certain conditions to reveal reactive functional groups, facilitating the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Research:
(3R)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylic acid is utilized in pharmaceutical research for the development of new drugs. Its unique structure and functional group protection make it a valuable tool for exploring novel therapeutic agents and advancing drug discovery.

Upstream product

• 146232-49-7 (4R)-3-(5-bromovaleryl)-4-phenylmethyl-2-oxazolidinone 
• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 1219114-45-0 di-tert-butyl 3-[(S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]hexahydropyridazine-1,2-dicarboxylate 
• 4509-90-4 5-bromovaleroyl chloride 
• 146232-50-0 (4R)-3-<(3R)-N,N'-bis(t-butoxycarbonyl)hexahydropyridazine-3-carboxy>-4-phenylmethyl-2-oxazolidinone 

Downstream Products

• 174497-80-4 methyl (3R)-N,N'-bis-(t-butoxycarbonyl)hexahydropyridazine-3-carboxylate 
• 32655-45-1 (3R)-N¹-(2,4-dinitrophenyl)hexahydropyridazine-3-carboxylic acid 
• 32655-46-2 methyl (3R)-N¹-(2,4-dinitrophenyl)hexahydropyridazine-3-carboxylate 
• 275805-33-9 (R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester 
• 275805-35-1 (R)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester 

Relevant academic research and scientific papers

Total synthesis and structure elucidation of JBIR-39: A linear hexapeptide possessing piperazic acid and γ-hydroxypiperazic acid residues

The total synthesis and stereochemical structural elucidation of JBIR-39, containing four nonproteinogenic piperazic acid (Piz) residues, is reported. The synthesis includes Sc(OTf)3-catalyzed acylation of a Piz(γ-OTBS) derivative with piperazi

Synthesis of the southern tripeptide (C1-N12) of sanglifehrins using asymmetric organocatalysis

The tripeptide southern region of the novel cyclophilin binding natural product macrolides, namely sanglifehrins, is synthesized involving asymmetric organocatalysis as chirality-inducing step. List's asymmetric α-amination was used in the synthesis of th

Synthesis of the tripeptide domain of sanglifehrins using asymmetric phase-transfer catalysis

The tripeptide (S)-valinyl-(S)-m-hydroxyphenylalanyl-(3S)-piperazate common to immunosuppressant sanglifehrins was synthesized from the constituent amino acid residues in nine steps and 42% overall yield. A key construction was the installation of (S) absolute configuration in m-hydroxyphenylalanine using asymmetric phase-transfer catalysis in the presence of N-(1-naphthyl) cinchonidinium bromide. Cbz-protected (S)-valine was first coupled to the amino group of (S)-m-triisopropylsilyloxyphenylalanine tert-butyl ester, and the resulting dipeptide after ester cleavage was linked to (3S)-methyl piperazate.

Total synthesis of NW-G01, a cyclic hexapeptide antibiotic, and 34-epi-NW-G01

NW-G01, a cyclic hexapeptide antibiotic, and 34-epi-NW-G01 were synthesized by the highly stereoselective convergent approach for the first time, thereby unambiguously determining the absolute structure of NW-G01.

Enantioselective synthesis of (3R)- and (3S)-piperazic acids. The comparative unimportance of DMPU mediated retro-hydrazination

In response to a recent literature report by Decicco and Leathers, the work of Hale, Delisser, and Manaviazar (1992) on the asymmetric synthesis of (3R)- and (3S)-piperazic acids has been reinvestigated, and the originally claimed product yields fully substantiated. The claims made in reference 13 about the proportions of cyclised product 6 and starting bromide 20 isolated from the low temperature electrophilic hydrazination-nucleophilic cyclisation of 20 with di-t-butylazodicarboxylate (DBAD) and DMPU as an additive are inaccurate. The retro-hydrazination reaction that they claim is problematic when DMPU is added to the hydrazinated reaction mixture has been demonstrated not to have a seriously detrimental effect on cyclisation product yield and to be unimportant. The other main ion of reference 13, that the electrophilic hydrazination and nucleophilic cyclisation of 20 gives 6 in 91% isolated yield when n-Bu4NI is employed as an additive (instead of DMPU) has also been shown to be in error. We have carefully repeated a scaled-down version of the n-Bu4NI catalysed procedure and have found that 6 is generally isolated in yields of 50-56% after flash chromatography. We have concluded that n-Bu4NI does not significantly increase the yields of cyclisation products 6 or 17 when it is employed as a cyclisation additive. Herein, we report details of our two preferred 'crude' experimental procedures for preparing the enantiomers of piperazic acid in high optical purity, neither of which requires chromatographic purification of the reaction intermediates en route. Both these preferred 'crude' methods for preparing 11 and 19 have been consistently reproduced many times in these laboratories over the past few years. In our view, they remain the most expedient and highest yielding methods currently available for obtaining 11 and 19 in high optical purity.

AZINOTHRICIN SYNTHETIC STUDIES. 1. EFFICIENT ASYMMETRIC SNTHESES OF (3R)- AND (3S)-PIPERAZIC ACIDS

A convenient asymmetric synthesis of both (3R)-and (3S)-piperazic acids has been developed that is based on electrophilic hydrazination of a chiral bromovaleryl carboximide enolate with di-tert-butyl azodicarboxylate, followed by subsequent intramolecular