159213-18-0

Basic information

• Product Name: (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate
• Synonyms: (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate;ethyl 3-amino-2,5-dioxopyrrolidine-3-carboxylate
• CAS NO: 159213-18-0
• Molecular Formula: C7H10N2O4
• Molecular Weight: 186.1653
• EINECS: -0
• Mol File: 159213-18-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 125-126 °C
• Boiling Point: 365.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.350±0.06 g/cm3(Predicted)
• PKA: 7.70±0.50(Predicted)
• CAS DataBase Reference: (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate(159213-18-0)
• EPA Substance Registry System: (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate(159213-18-0)

Safety Data

• Hazardous Substances Data: 159213-18-0(Hazardous Substances Data)

Usage

General Description

The chemical (R)-ethyl 3-amino-2,5-dioxopyrrolidine-3-carboxylate is a compound with the molecular formula C8H12N2O5. It is a derivative of pyrrolidine and contains an amino group, a carboxylate ester group, and a dioxopyrrolidine ring. (R)-ethyl 3-aMino-2,5-dioxopyrrolidine-3-carboxylate is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. Its chirality is specified by the (R) designation, indicating that it has a specific spatial arrangement of atoms. This chemical is an important building block in organic synthesis and has diverse applications in the pharmaceutical and chemical industries.

Upstream product

• 140405-41-0 ethyl 1-benzyl-2,5-dioxopyrrolidine-3-carboxylate 
• 105-53-3 diethyl malonate 
• 96905-68-9 3-ethoxycarbonylpyrrolidin-2,5-dione 
• 1239129-13-5 diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate 
• 1239129-17-9 (R)-diethyl 2-benzyloxycarbonylamino-2-carbamoylsuccinate 
• 1239129-15-7 (R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonylsuccinate 
• 3005-66-1 diethyl 2-benzyloxycarbonylaminomalonate 
• 147194-10-3 ethyl 3-benzyloxycarbonylamino-2,5-dioxopyrrolidine-3-carboxylate 
• 952656-32-5 ethyl (R)-3-hydrazinyl-2,5-dioxopyrrolidine-3-carboxylate hydrochloride 
• 159213-17-9 (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide 

Downstream Products

• 147254-64-6 ranirestat 

Relevant articles and documents

A novel method of producing the key intermediate ASI-2 of ranirestat using a porcine liver esterase (PLE) substitute enzyme

(R)-2-amino-2-ethoxycarbonylsuccinimide (ASI-2) is a key intermediate used in the pharmaceutical industry and is valuable for the industrial synthesis of ranirestat, which is a potent aldose reductase inhibitor. ASI-2 was synthesized in a process combining chemical synthesis and bioconversion. Bioconversion in this study is a key reaction, since optically active carboxylic acid derivative ((R)-1-ethyl hydrogen 3-benzyloxycarbonylamino-3-ethoxycarbonyl-succinate, Z-MME-AE) is synthesized from a prochiral ester, diethyl 2-benzyloxycarbonyla-mino-2-ethoxycarbonylsuccinate, Z-MDE-AE, at a theoretical yield of 100%. Upon screening for microorganisms that asymmetrically hydrolyze Z-MDE-AE, Bacillus thuringiensis NBRC13866 was found. A novel esterase EstBT that produces Z-MME-AE was purified from Bacillus thuringiensis NBRC13866 and was stably produced in Escherichia coli JM109 cells. Using EstBT rather than porcine liver esterase (PLE), ASI-2 was synthesized with a 17% higher total yield by a novel method, suggesting that the esterase EstBT is a PLE substitute enzyme and therefore, may be of interest for future industrial applications.

First Kilogram-Scale Application of the Lanthanum Catalyzed Asymmetric Amination to Synthesis of the Chiral Succinimide Derivative, A Key Intermediate for the Preparation of AS-3201

The process development of ethyl-(R)-3-amino-2,5-dioxopyrrolidine-3-carboxylate (2), the chiral intermediate for the manufacture of AS-3201 (1), is described. A practical and scalable Shibasaki asymmetric amination that generates the chiral quaternary center was developed and demonstrated on kilogram scale. A safe, convenient, and large-scale hydrogenation of the hydrazine intermediate was also developed.

SUCCINIC ACID DIESTER DERIVATIVE, PROCESS FOR PRODUCTION THEREOF, AND USE OF THE DERIVATIVE IN THE PRODUCTION OF PHARMACEUTICAL PREPARATION

The present invention provides with a process of preparing an optically active succinimide derivative, which is a key intermediate for production of ranirestat. A compound (3) is easily prepared by treating the derivative of succinic acid diester of the formula (2): wherein R1 is an amino group protected with a group removed by hydrogenolysis or a tert-butoxycarbonylamino group and R2 is an ethyl group optionally substituted with one or two methyl group(s) at α-position, provided that R2 is not a tert-butyl group when R1 is a tert-butoxycarbonylamino group; with alkali metal alkoxide and the compound (3) can be an important intermediate for production of ranirestat.