52989-50-1

Basic information

• Product Name: isopropyl 5-oxo-L-prolinate
• Synonyms: isopropyl 5-oxo-L-prolinate;5-Oxo-L-proline 1-methylethyl ester;L-Pyroglutamic acid isopropyl ester
• CAS NO: 52989-50-1
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19372
• EINECS: 258-285-4
• Mol File: 52989-50-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 314.5°Cat760mmHg
• Flash Point: 144°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 0.000463mmHg at 25°C
• Refractive Index: 1.465
• PKA: 14.84±0.40(Predicted)
• CAS DataBase Reference: isopropyl 5-oxo-L-prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: isopropyl 5-oxo-L-prolinate(52989-50-1)
• EPA Substance Registry System: isopropyl 5-oxo-L-prolinate(52989-50-1)

Safety Data

• Hazardous Substances Data: 52989-50-1(Hazardous Substances Data)

Usage

General Description

Isopropyl 5-oxo-L-prolinate is a chemical compound with the molecular formula C8H13NO3. It is a derivative of proline, a non-essential amino acid, and is commonly used as a chiral building block in organic synthesis. isopropyl 5-oxo-L-prolinate has a unique structure with a 5-oxo group attached to the L-proline backbone and isopropyl group attached to the nitrogen atom. Isopropyl 5-oxo-L-prolinate is used in pharmaceutical research and drug development, as well as in the production of fine chemicals and advanced materials. Its chiral nature and diverse reactivity make it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other complex organic compounds.

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 articles and documents

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.

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.

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.