51814-19-8

Basic information

• Product Name: Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate
• Synonyms: Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate;ETHYL 1-N-CBZ-4-OXO-PYRROLIDINE-3-CARBOXYLATE;1-benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate;4-Oxopyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester;1-Cbz-4-oxo-3-Pyrrolidinecarboxylic acid ethyl ester
• CAS NO: 51814-19-8
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.3
• Product Categories: Amino Acids and Derivatives;Carbonyl Compounds
• Mol File: 51814-19-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 433.1 °C at 760 mmHg
• Flash Point: 215.8 °C
• Appearance: /
• Density: 1.274 g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 11.17±0.20(Predicted)
• CAS DataBase Reference: Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate(51814-19-8)
• EPA Substance Registry System: Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate(51814-19-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 51814-19-8(Hazardous Substances Data)

Usage

General Description

Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate is a chemical compound with the molecular formula C15H19NO5. It is commonly used in organic synthesis as a building block for the production of various pharmaceuticals and agrochemicals. Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate is known for its ability to react with other chemicals to form new substances with desirable properties. It is also used in the development of new materials and as a key intermediate in the production of fine chemicals. Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate is an important molecule in the field of organic chemistry and is widely employed in the synthesis of complex organic compounds.

InChI:InChI=1/C15H17NO5/c1-2-20-14(18)12-8-16(9-13(12)17)15(19)21-10-11-6-4-3-5-7-11/h3-7,12H,2,8-10H2,1H3

Upstream product

• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 140-88-5 ethyl acrylate 
• 51814-17-6 ethyl N-benzoxycarbonyl-N-(2-ethoxcarbonylethyl)glycinate 
• 501-53-1 benzyl chloroformate 
• 1245646-09-6 C₁₆H₂₁NO₆ 

Downstream Products

• 886435-83-2 4-methoxyimino-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester 
• 1428243-26-8 (3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate 
• 1268520-70-2 (3R,4S)-1-tert-butoxycarbonyl-4-ethyl-pyrrolidin-3-carboxylic acid 

Relevant articles and documents

Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib

Process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, optimization of the imidazole cyclization, and in-depth understanding of the formation of the urea moiety at the final stage are discussed.

PROCESS FOR PRODUCTION OF 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE AND INTERMEDIATE FOR THE PRODUCTION

An industrially advantageous process for the production of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof that is useful as an intermediate for the production of novel antimicrobial agents 10-(3-cyclopropylaminomethyl-4-fluoropyrrolidinyl)pyridobenzox azine carboxylic acid derivatives. Highly stereoselective asymmetric hydrogenation of 1-protected-4-alkoxycarbonyl-3-oxopyrrolidine, followed by ester hydrolysis, followed by amidation with cyclopropylamine gives crude crystals. The crude crystals are purified by recrystallization to give a novel compound (3R,4S)-1-protected-3-cyclopropylcarbamoyl-4-hydroxypyrrolidin e or an enantiomer thereof at high optical purity. The use of these intermediates enables industrial production of high-quality products of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof. The process is highly simple and can produce the desired products at high purity and stable yields.

8A,9-dihydro-4aH-isothiazolo[5,4-b]quinoline-3,4-diones and related compounds as anti-infective agents

The invention provides compounds and salts of Formula I and Formula II: which possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula I and Formula II. The variables n, m, p, RA, RB, A1, R2, R3, R5, R6, R7, A8 and R9 are defined herein. Certain compounds of Formula I and Formula II disclosed herein are potent and/or selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in eukaryotes.