84677-05-4

Usage

Uses

Used in Pharmaceutical Research and Development:
Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester is employed as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester serves as a versatile building block for creating a range of bioactive molecules. Its functional groups enable various chemical reactions, facilitating the synthesis of complex organic compounds.
Used in Drug Design and Medicinal Chemistry:
Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester is utilized in drug design and medicinal chemistry for the development of novel therapeutic agents. Its unique properties and reactivity make it a promising candidate for the creation of drugs targeting specific diseases and conditions.
Used in Chemical Research:
In the realm of chemical research, Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester is employed to study the properties and reactivity of cyclopropane-based compounds. This research contributes to a deeper understanding of the chemical behavior of such compounds and their potential applications in various fields.
Used in the Development of Bioactive Molecules:
Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester is used in the development of bioactive molecules with potential applications in medicine, agriculture, and other industries. Its unique structure and functional groups allow for the creation of molecules with specific biological activities, such as antimicrobial, antiviral, or anti-inflammatory properties.

Upstream product

• 15159-67-8 (2S)-2-benzyloxycarbonylamino-4-bromo-butyric acid methyl ester 
• 100-39-0 benzyl bromide 
• 84677-06-5 (benzyloxycarbonylamino)cyclopropanecarboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 501-53-1 benzyl chloroformate 
• 72784-42-0 methyl 1-aminocyclopropane-1-carboxylate hydrochloride 
• 76338-91-5 2-<(benzyloxycarbonyl)amino>-4-bromobutanoic acid methyl ester 

Downstream Products

• 210576-30-0 Methyl 1-(N-benzyloxycarbonyl-N-methyl)aminocyclopropane-1-carboxylic acid 
• 119111-66-9 1-methylamino-cyclopropanecarboxylic acid methyl ester 
• 84677-06-5 (benzyloxycarbonylamino)cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement

An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.

Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors

An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)2borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 μM.

1-Aminocylopropane-1-carboxylic acid derivatives as ligands at the glycine-binding site of the N-methyl-D-aspartate receptor

Several 1-aminocyclopropane-1-carboxylic acid derivatives were prepared and tested for activity at the glycine-binding site of the N-methyl-D- aspartate (NMDA) receptor complex. Structural modifications involved the amino group, the carboxylic function or

Facile new method for preparation of optically active protected proline

Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.

A Simple Synthesis of 1-Aminocyclopropane-1-carboxylic Acid

Conversion of N-carbobenzyloxy-L-glutamic acid α-methylester (Z-L-glu(OH)OCH3, 1) into the bromo derivative 2 and subsequent γ-elimination by the use of sodium hydride leads to the fully protected synthon 3 in good yields.Deprotection by sodium hydroxide and hydrogenolysis yields almost quantitively the key substance 5.