94985-27-0

Basic information

• Product Name: 1-BENZYL-AZETIDINE-3-CARBOXYLIC ACID
• Synonyms: 1-Benzyl-3-azetidinecarboxylic acid;3-Azetidinecarboxylic acid, 1-(phenylmethyl)-;1-Benzylazetane-3-carboxylic acid, 1-Benzyl-3-carboxyazetidine;1-Benzylazetidine-3-carboxylicacid97%;1-BENZYL-AZETIDINE-3-CARBOXYLIC ACID
• CAS NO: 94985-27-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• Mol File: 94985-27-0.mol

Chemical Properties

• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 151.9 °C
• Appearance: /
• Density: 1.253 g/cm³
• Vapor Pressure: 8.13E-05mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: 2-8°C
• PKA: 2.72±0.20(Predicted)
• CAS DataBase Reference: 1-BENZYL-AZETIDINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-AZETIDINE-3-CARBOXYLIC ACID(94985-27-0)
• EPA Substance Registry System: 1-BENZYL-AZETIDINE-3-CARBOXYLIC ACID(94985-27-0)

Safety Data

• Hazardous Substances Data: 94985-27-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzyl-azetidine-3-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic benefits.
Used in Organic Synthesis:
As a building block in organic synthesis, 1-Benzyl-azetidine-3-carboxylic acid is utilized for creating a variety of organic compounds, expanding the scope of chemical research and product development.
Used in Antimicrobial Applications:
1-Benzyl-azetidine-3-carboxylic acid is studied for its potential use in treating bacterial and viral infections, leveraging its antimicrobial properties to combat various pathogens.
Used in Antioxidant and Anti-Inflammatory Applications:
Due to its antioxidant and anti-inflammatory properties, 1-Benzyl-azetidine-3-carboxylic acid has potential applications in medical and cosmetic industries, where it can be used to develop products that promote skin health and treat inflammation-related conditions.
Used in Research and Development:
In the scientific community, 1-Benzyl-azetidine-3-carboxylic acid serves as a valuable compound for research and development, enabling the exploration of new chemical reactions and the discovery of novel therapeutic agents.

InChI:InChI=1/C11H13NO2/c13-11(14)10-7-12(8-10)6-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,14)

Upstream product

• 94985-26-9 1-benzyl-3-cyanoazetidine 
• 99025-94-2 (1-benzylazetidin-3-yl)methanol 
• 106014-87-3 1-(phenylmethyl)-3,3-azetidinedicarboxylic acid 

Downstream Products

• 36476-78-5 3-azetidinecarboxylic acid 
• 99025-94-2 (1-benzylazetidin-3-yl)methanol 
• 1233923-94-8 1-benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylazetidine-3-carboxamide 

Relevant articles and documents

Production methods of nitrogen heterocyclic carboxylic acid intermediate and 3-azetidine carboxylic acid

The invention discloses production methods of a nitrogen heterocyclic carboxylic acid intermediate and 3-azetidine carboxylic acid, and relates to the technical field of pharmaceutical and chemical industry. The production method of the nitrogen heterocyclic carboxylic acid intermediate used for producing the 3-azetidine carboxylic acid comprises the steps of mixing a nitrogen heterocyclic compound and a Wittig reaction agent, carrying out a Wittig reaction, and conducting separation to obtain a nitrogen heterocyclic formaldehyde intermediate; and subjecting the nitrogen heterocyclic formaldehyde intermediate to an oxidation reaction, and conducting separation to obtain the nitrogen heterocyclic carboxylic acid intermediate, wherein the nitrogen heterocyclic compound is selected from at least one of 1-benzhydrylazetidin-3-one, 1-benzylazetidin-3-one, 1-Boc-3-azetidinone and 1-acetylazetidin-3-one. According to the production method of the 3-azetidine carboxylic acid, the nitrogen heterocyclic carboxylic acid intermediate is subjected to hydrogenolysis, a production cycle is short, a production process is safe and reliable, the production cost is low, the purity is higher than 98%,and the yield can reach 82.8%.

NEW TETRACYCLINE DERIVATIVES AS ANTIINFECTIVE AGENTS

In accordance with one embodiment, the present invention provides a compound of general formula (I), stereoisomers thereof and/or its pharmaceutically acceptable salts thereof, which have antibacterial activity; with methods of treating infectious diseases in warm blooded animals employing these new compounds.

PROCESS FOR MAKING AZETIDINE-3-CARBOXYLIC ACID

The present invention is directed to an improved process for synthesizing azetidine-3-carboxylic acid, comprising triflating diethylbis(hydroxymethyl)malonate followed by azetidine ring-formation by intramolecular cyclization using an amine, decarboxylation to give the mono acid azetidine and hydrogenation to give the title compound. Azetidine-3-carboxylic acid is useful as an intermediate for making certain S1P?1#191/Edg1 receptor agonists, which are immunosupressive agents.

A practical process for the preparation of azetidine-3-carboxylic acid

A practical and convenient synthesis of azetidine-3-carboxylic acid (1) that proceeded in 55% overall yield from commercially available diethylbis(hydroxymethyl)malonate (3) is reported. Azetidine ring-formation was achieved in high yield by cyclization of bistrifiate of the diol (3) and benzylamine. Decarboxylation under carefully pH-controlled conditions gave the mono acid azetidine that was hydrogenated to give the title compound.

Catalytic hydrogenolysis

Preparation of azetidine-3-carboxylic acid or a salt thereof from N-benzylazetidine-3-carboxylic acid or a salt thereof by catalytically hydrogenating the N-benzylazetidine-3-carboxylic compound in the presence of water, formate ions, and ammonium and/or alkylammonium ions. Novel ammonium and alkylammonium salts are claimed.

Process for preparing azetidine derivatives; and intermediates therein

Process for the preparation of a compound of formula or a salt thereof STR1 wherein R1 represents a hydrogen atom or a group of formula R2 SO2 or phenyl--CH(R3)--wherein R2 represents a phenyl, tolyl or C1-4 alkyl group and R3 represents a hydrogen atom or a phenyl of C1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula STR2 wherein R4 represents a group of formula R2 SO2 or phenyl--CH(R3)--and R5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R1 represents a hydrogen atom, by deprotection of the N-atom. Also, novel N-substituted azetidine carboxylate derivatives of the formula STR3 wherein X represents a group CH2 OH or COOY where Y represents a hydrogen or an alkali or alkaline earth metal atom.

Azetidine-3-carboxylic acid derivatives

The novel ester, N-benzylazetidine-3-carboxylic acid methyl ester and its use in the preparation of the corresponding free acid by a process which comprises reacting N-benzyl-3-cyanozetidine with methanol and hydrolyzing the resulting methyl ester with hot water.

Preparation of 1-benzylazetidine-3-ol derivatives

A process for the preparation of 1-substituted azetidin-3-ol derivatives of the formula: STR1 in which R1 represents a hydrogen atom or an alkyl, aryl or aralkyl group in which the alkyl moiety contains up to eight carbon atoms, by cyclizing a solution in triethylamine of an aminoalcohol of the formula: STR2 in which Hal represents a halogen atom and the use of such derivatives as intermediates for the preparation of azetidine-3-carboxylic acid derivatives.

A process for the preparation of an azetidine-3-carboxylic acid or salt thereof

The invention relates to a process for the preparation of an azetidine-3-carboxylic acid of the formula I: or a salt thereof, wherein R1 represents a hydrogen atom, a C1-6alkyl or C3-8cycloalkyl group or a group phenyl-CH(R3)- wherein R3 represents a hydrogen atom, a phenyl or an alkyl group of 1-4 carbon atoms, which process comprises reacting an azetidine of the formula II: wherein R1 has the meanings defined above, and X represents a hydrogen atom, a carboxyl or a group, with an alkali metal base at a temperature of from 150 to 300°C in the presence of a catalyst comprising a metal of the Group IIB of the Periodic System and/or a compound of said metal, and if desired converting the obtained azetidine-3-carboxylic acid salt into the corresponding acid; and to novel alkali, alkaline earth and quaternary ammonium salts of such acids.

Preparation of 1-benzylazetidin-3-ol

1-Benzylazetidin-3-ol, a precursor to 3-carboxyazetidine, is prepared by heating N-benzyl-3-amino-1-chloropropan-2-ol in an aqueous medium, optionally treating the resulting hydrochloride salt with an alkali metal base.