52989-50-1

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
Isopropyl 5-oxo-L-prolinate is used as a chiral building block for the synthesis of pharmaceuticals, agrochemicals, and other complex organic compounds. Its chiral nature and diverse reactivity make it a valuable intermediate in the development of new drugs and therapeutic agents.
Used in Production of Fine Chemicals and Advanced Materials:
Isopropyl 5-oxo-L-prolinate is used as a key intermediate in the production of fine chemicals and advanced materials. Its unique structure and reactivity contribute to the development of innovative products with specialized properties and applications.

InChI:InChI=1/C8H13NO3/c1-5(2)12-8(11)6-3-4-7(10)9-6/h5-6H,3-4H2,1-2H3,(H,9,10)/t6-/m0/s1

Upstream product

• 56-85-9 L-glutamine 
• 67-63-0 isopropyl alcohol 
• 56-86-0 L-glutamic acid 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 35418-16-7 L-t-butyl pyroglutamate 
• 158775-11-2 (S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester 
• 529483-98-5 t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate 

Relevant academic research and scientific papers

Formal Synthesis of (-)-Quinagolide: Diastereoselective Ring Expansion via a Bicyclic Aziridinium Ion Strategy to Access the Octahydrobenzo[ g]quinoline Architecture

The diastereoselective formal synthesis of (-)-quinagolide, a D2 receptor agonist, has been achieved. The synthesis started from l-pyroglutamic acid and relied on utilization of (a) a stereospecific catalytic hydrogenation and diastereoselective Horner-Emmons-Michael cascade to obtain functionalized prolinate, (b) a Lewis acid mediated Pummerer cyclization to construct a tricyclic fused ring system, and (c) a diastereoselective ring expansion via a bicyclic aziridinium intermediate to access the required 3-substituted piperidine scaffold.

Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization

Dimeric cyclotryptamine alkaloids typically feature vicinal all-carbon quaternary stereocenters and four nitrogen atoms. In comparison with the actual biosynthetic tryptophan derivatives, we designed the 2N-featured monomer 7, aiming to construct vicinal all-carbon quaternary stereocenters via a one-step dimerization process to access the 4N-featured isomeric members of this family. In this work, we disclose the first synthetic route to access the skeleton of (-)-isocalycanthine, featuring an iron-catalyzed oxidative dimerization reaction in a catalytic single-step operation with an overwhelming control of the absolute and relative stereochemistry. This strategy has been successfully applied to the total synthesis of (-)-calycanthine and 16 isocalycanthine derivatives, which demonstrates a new synthetic pathway for dimeric cyclotryptamine alkaloids.

METHOD OF PREPARING A DON PRODRUG FROM L-PYROGLUTAMIC ACID

The present disclosure provides a method of preparing a compound of Formula I, wherein R1 is C1-C4 alkyl; R2 is C1-C4 alkyl; and R3 is selected from the group consisting of C1-C6 alkyl, (aryl)alkyl, and (heteroaryl)alkyl in >95% chemical purity and >95% enantiomeric excess.

Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides

Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.

Synthesis and bioactivities evaluation of L-pyroglutamic acid analogues from natural product lead

A series of L-pyroglutamic acid analogues from natural product lead were designed and synthesized, as well as their antifungal activities against Phytophthora infestans, neuritogenic activities, antibacterial activities and anti-inflammatory activities are described. The bioassays and SAR study showed that the majority of L-pyroglutamic acid esters have a significant antifungal activity against P. infestans, especially 2d and 2j demonstrated the best activities with EC50 values of 1.44 and 1.21 μg mL?1, which were about seven times that of commercial azoxystrobin (7.85 μg mL?1). Moreover, compounds 2e, 2g and 4d displayed anti-inflammatory activity against LPS-induced NO production in BV-2 microglial cells; neuritogenic activity in NGF-induced PC-12 cells is the same activity. This study demonstrates that compounds 2d and 2j are potential drugs to control P. infestans.

CALPAIN MODULATORS AND METHODS OF PRODUCTION AND USE THEREOF

The present technology relates to compounds, kits, compositions, and methods useful for the treatment of fibrotic disease. In some aspects, the present technology provides for treatment of various diseases or disorders associated or mediated, at least in part, by calpains, such as CAPN1, CAPN2, and/or CAPN9. The present technology is generally applicable to compounds which inhibit myofibroblast differentiation.

Compounding method for LCZ696 midbody

The invention discloses a compounding method for a LCZ696 midbody. The compounding route is as follows: wherein R1 is Me, Et or i-Pr; X is Cl, Br or I; R2 is Ms, Ts or Tf. According to the compounding method for the LCZ696 midbody disclosed by the invention, the methylating difficulty is reduced, the midbody is configured and overturned through the consequent reaction, the proportion of the required configuration is greatly increased, the product yield, purity and use ratio are increased and the industrial large-scale production is benefited.

Inhibitors of Hepatitis C Virus

Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS

Macrocyclic peptides having the general formula (I): are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Inhibitors of Hepatitis C Virus

Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.