153080-81-0

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S,4R)-
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S,4R)-;(2S,4R)-1-tert-Butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate
• CAS NO: 153080-81-0
• Molecular Formula: C₁₅H₂₃NO₅
• Molecular Weight: 297.34682
• Mol File: 153080-81-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S,4R)-(153080-81-0)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S,4R)-(153080-81-0)

Safety Data

• Hazardous Substances Data: 153080-81-0(Hazardous Substances Data)

Usage

Type of Compound

Ester derivative of pyrrolidinedicarboxylic acid

Side Chain

5-oxo-4-(2-propen-1-yl)

Substituents

Isobutyl (1,1-dimethylethyl) at position 1
Ethyl at position 2

Stereochemical Configuration

(2S,4R)

Pharmaceutical

Treating neurological disorders and cancer

Industrial

Building block in the synthesis of organic compounds for various processes

Biological Activity

The stereochemical configuration (2S,4R) is crucial for its effectiveness in potential applications

Structure

The compound consists of a pyrrolidine ring with two carboxylic acid groups, an ester group, and a 5-oxo-4-(2-propen-1-yl) side chain

Functional Groups

Carboxylic acid, ester, and alkene groups are present in the molecule

Chirality

The molecule has two chiral centers, which contribute to its stereochemical configuration (2S,4R)

Upstream product

• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 106-95-6 allyl bromide 

Downstream Products

• 942144-12-9 tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate 
• 942145-39-3 methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate 
• 1013937-63-7 methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate 
• 942144-13-0 (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 942144-14-1 (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 942144-35-6 (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 942144-36-7 (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(methylsulfonyloxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 942144-34-5 (S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate 
• 942144-43-6 tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate 
• 942145-23-5 (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate 
• 942145-24-6 tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate 
• 942145-26-8 tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate 
• 942145-27-9 tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate 
• 1374570-31-6 C₃₀H₄₄N₂O₁₀ 

Relevant articles and documents

Synthesis and analysis of 4-(3-fluoropropyl)-glutamic acid stereoisomers to determine the stereochemical purity of (4S)-4-(3-[18F]fluoropropyl)-L-glutamic acid ([18F]FSPG) for clinical use

(4S)-4-(3-[18F]Fluoropropyl)-L-glutamic acid ([18F]FSPG) is a positron emission tomography (PET) imaging agent for measuring the system xC - transporter activity. It has been used for the detection of various cancers and metastasis in clinical trials. [18F]FSPG is also a promising diagnostic tool for evaluation of multiple sclerosis, drug resistance in chemotherapy, inflammatory brain diseases, and infectious lesions. Due to the very short half-life (110 min) of 18F nuclide, [18F]FSPG needs to be produced on a daily basis; therefore, fast and efficient synthesis and analytical methods for quality control must be established to assure the quality and safety of [18F]FSPG for clinical use. To manufacture cGMP-compliant [18F]FSPG, all four nonradioactive stereoisomers of FSPG were prepared as reference standards for analysis. (2S,4S)-1 and (2R,4R)-1 were synthesized starting from protected L- and D-glutamate derivatives in three steps, whereas (2S,4R)-1 and (2R,4S)-1 were prepared in three steps from protected (S)- and (R)-pyroglutamates. A chiral HPLC method for simultaneous determination of four FSPG stereoisomers was developed by using a 3-cm Chirex 3126 column and a MeCN/CuSO4(aq) mobile phase. In this method, (2R,4S)-1, (2S,4S)-1, (2R,4R)-1, and (2S,4R)-1 were eluted in sequence with sufficient resolution in less than 25 min without derivatization. Scale-up synthesis of intermediates for the production of [18F]FSPG in high optical purity was achieved via stereo-selective synthesis or resolution by recrystallization. The enantiomeric excess of intermediates was determined by HPLC using a Chiralcel OD column and monitored at 220 nm. The nonradioactive precursor with >98% ee can be readily distributed to other facilities for the production of [18F]FSPG. Based on the above accomplishments, cGMP-compliant [18F]FSPG met the acceptance criteria in specifications and was successfully manufactured for human use. It has been routinely prepared and used in several pancreatic ductal adenocarcinoma metastasis-related clinical trials.

Discovery of VTP-27999, an alkyl amine renin inhibitor with potential for clinical utility

Structure guided optimization of a series of nonpeptidic alkyl amine renin inhibitors allowed the rational incorporation of additional polar functionality. Replacement of the cyclohexylmethyl group occupying the S1 pocket with a (R)-(tetrahydropyran-3-yl)

RENIN INHIBITORS

Described are compounds that bind to aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also described are methods of use of the compounds described herein in ameliorating or treating aspartic protease related disorders in a subject in need thereof.