74761-41-4

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI)
• Synonyms: 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI);(2S)-1,2-Pyrrolidinedicarboxylic acid 1-Methyl ester;1-(methoxycarbonyl)-L-proline;MFCD12795354;(S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS NO: 74761-41-4
• Molecular Formula: C₇H₁₁NO₄
• Molecular Weight: 173.17
• Product Categories: PYRROLE
• Mol File: 74761-41-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 317.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.335±0.06 g/cm3(Predicted)
• PKA: 4.00±0.20(Predicted)
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI)(74761-41-4)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI)(74761-41-4)

Safety Data

• Hazardous Substances Data: 74761-41-4(Hazardous Substances Data)

Usage

Description

1,2-Pyrrolidinedicarboxylic acid, 1-methylester, (2S)-(9CI), also known as N-Methyl-D-proline or N-Methyl-D-pyroglutamate, is a chiral chemical compound with the molecular formula C7H11NO4. It is a derivative of pyrrolidine and possesses a unique structure and properties. 1,2-Pyrrolidinedicarboxylicacid,1-methylester,(2S)-(9CI) is characterized by its (2S) stereochemistry, which is crucial for its potential applications in various fields.

Uses

Used in Pharmaceutical Synthesis:
1,2-Pyrrolidinedicarboxylic acid, 1-methylester, (2S)-(9CI) is used as an intermediate in the synthesis of pharmaceuticals for its unique structure and properties. Its chiral nature allows for the development of enantiomer-specific drugs, which can have different biological activities and reduce potential side effects.
Used in Organic Chemistry:
In the field of organic chemistry, 1,2-Pyrrolidinedicarboxylic acid, 1-methylester, (2S)-(9CI) serves as a versatile building block for the synthesis of various organic compounds. Its reactivity and functional groups enable the formation of diverse chemical entities, contributing to the advancement of organic synthesis and the discovery of new molecules with potential applications.
Used in Biochemistry Research:
1,2-Pyrrolidinedicarboxylic acid, 1-methylester, (2S)-(9CI) is utilized in biochemistry research to study enzyme mechanisms, protein structures, and other biological processes. Its unique stereochemistry and functional groups allow researchers to probe the selectivity and specificity of enzymes and other biomolecules, leading to a better understanding of biological systems and the development of novel therapeutic agents.

Upstream product

• 79-22-1 methyl chloroformate 
• 147-85-3 L-proline 

Downstream Products

• 45736-33-2 (S)-proline-N-carboxyanhydride 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 86953-80-2 methyl 2-hydroxy-1-pyrrolidinecarboxylate 
• 56475-88-8 methyl 2-methoxypyrrolidine-1-carboxylate 
• 76470-01-4 methyl 2-(2-oxocyclohexyl)-1-pyrrolidinecarboxylate 
• 97316-71-7 methyl 2-(2-propenyl)pyrrolidinecarboxylate 
• 380367-23-7 -methyl 2-(2-oxopropyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 154-06-3 2-Amino-3-(5-methyl-1H-indol-3-yl)-propionic acid 
• 56-69-9 5-hydroxy-L-tryptophan 
• 154-07-4 5-chloro-L-tryptophan 
• 6548-09-0 5-bromo-L-tryptophan 
• 2504-22-5 5-methoxy-L-tryptophan 
• 93299-38-8 5-bromo-L-tryptophan methyl ester 
• 89434-13-9 5-benzyloxy-N_b-methoxycarbonyl-L-tryptophan methyl ester 

Relevant articles and documents

Discovery of AG-120 (Ivosidenib): A First-in-Class Mutant IDH1 Inhibitor for the Treatment of IDH1 Mutant Cancers

Somatic point mutations at a key arginine residue (R132) within the active site of the metabolic enzyme isocitrate dehydrogenase 1 (IDH1) confer a novel gain of function in cancer cells, resulting in the production of d-2-hydroxyglutarate (2-HG), an oncometabolite. Elevated 2-HG levels are implicated in epigenetic alterations and impaired cellular differentiation. IDH1 mutations have been described in an array of hematologic malignancies and solid tumors. Here, we report the discovery of AG-120 (ivosidenib), an inhibitor of the IDH1 mutant enzyme that exhibits profound 2-HG lowering in tumor models and the ability to effect differentiation of primary patient AML samples ex vivo. Preliminary data from phase 1 clinical trials enrolling patients with cancers harboring an IDH1 mutation indicate that AG-120 has an acceptable safety profile and clinical activity.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

Chirospecific synthesis of trans-2,5-disubstituted pyrrolidines via stereoselective addition of organocopper reagents to N-acyliminium ions

Reaction of the N-acyliminium ion precursor 1a (derived from S-proline via anodic methoxylation) with RCu in the presence of BF3·Et2O gives preferentially the trans adducts 2 (trans:cis ≥96:4). Using such a procedure, a general synthetic route to (2R, 5R)-trans-2,5-dialkylpyrrolidines has been developed, as exemplified by the chirospecific syntheses of the ant feromones trans 5-butyl-2-heptylpyrrolidine (10a), trans-5-ethyl-2-heptylpyrrolidine (10b) and trans-5-heptyl-2-(5-hexenyl)pyrrolidine (10c).