449758-77-4

Basic information

• Product Name: 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
• Synonyms: 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester;1-Boc-2-Methyl-2-azetidinecarboxylic acid;1-Boc-2-Methylazetidine-2-carboxylic acid;1-(tert-Butoxycarbonyl)-2-Methylazetidine-2-carboxylic acid;1,2-Azetidinedicarboxylic acid, 2-methyl-, 1-(1,1-dimethylethyl) ester;2-Methylazetidine-2-carboxylicacid,N-BOCprotected;-2-methylazetidine-2-carboxylic acid
• CAS NO: 449758-77-4
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.247
• Mol File: 449758-77-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.196
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester(449758-77-4)
• EPA Substance Registry System: 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester(449758-77-4)

Safety Data

• Hazardous Substances Data: 449758-77-4(Hazardous Substances Data)

Usage

General Description

2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester is a chemical compound used in the pharmaceutical industry as a building block for the synthesis of various drugs. It is an ester derived from 2-methyl-1,2-azetidinedicarboxylic acid and 1-(1,1-dimethylethyl) alcohol, and its molecular structure features a four-membered azetidine ring. 2-Methyl-1,2-azetidinedicarboxylic acid 1-(1,1-dimethylethyl) ester is highly reactive and is often used as a reagent in organic synthesis to introduce the azetidine ring into complex molecules. It is also used in the production of agrochemicals and specialty chemicals. However, due to its reactivity and potential toxicity, proper handling and disposal procedures must be followed when working with this compound.

Upstream product

• 1391077-71-6 1-benzyl-2-methylazetidine-2-carboxylic acid ethyl ester 
• 1391077-69-2 2-[benzyl-(2-chloroethyl)amino]propionic acid ethyl ester 
• 1391077-73-8 2-methylazetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 

Downstream Products

• 1198339-37-5 (R)-2-methylazetidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 1363402-35-0 2-methylazetidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 1391078-75-3 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester 
• 1391079-33-6 (R)-2-[(3-chloro-benzyl)-(3-methoxycarbonyl-propyl)-carbamoyl]-2-methyl-azetidine-1-carboxylic acid tert-butyl ester 
• 1391076-61-1 GLPG-0974 
• 1391078-19-5 4-[(3-chloro-benzyl)-((R)-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride 
• 1391078-74-2 C₂₉H₃₅N₃O₄S 
• 1391076-52-0 4-(benzothiazol-5-ylmethyl-{1-[2-(3,5-dimethylphenyl)acetyl]-2-methylazetidine-2-carbonyl}amino)butyric acid 
• 1391076-11-1 4-(benzofuran-6-ylmethyl-{1-[2-(3,5-dimethyl-phenyl)acetyl]-2-methyl-azetidine-2-carbonyl}amino)butyric acid 
• 1391073-47-4 1-[2-(3-iodo-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-methyl-amide 
• 1391078-66-2 C₂₁H₂₂ClIN₂O₂ 
• 1391075-19-6 1-(2-(benzo[b]thiophen-2-yl)acetyl)-N-(4-chlorobenzyl)-N,2-dimethylazetidine-2-carboxamide 
• 1391075-01-6 1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carboxylic acid (4-chlorobenzyl)methylamide 
• 1391075-41-4 1-(benzofuran-5-carbonyl)-N-(4-chlorobenzyl)-N,2-dimethylazetidine-2-carboxamide 

Relevant articles and documents

Discovery and optimization of an azetidine chemical series as a free fatty acid receptor 2 (FFA2) antagonist: From hit to clinic

FFA2, also called GPR43, is a G-protein coupled receptor for short chain fatty acids which is involved in the mediation of inflammatory responses. A class of azetidines was developed as potent FFA2 antagonists. Multiparametric optimization of early hits with moderate potency and suboptimal ADME properties led to the identification of several compounds with nanomolar potency on the receptor combined with excellent pharmacokinetic (PK) parameters. The most advanced compound, 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid 99 (GLPG0974), is able to inhibit acetate-induced neutrophil migration strongly in vitro and demonstrated ability to inhibit a neutrophil-based pharmacodynamic (PD) marker, CD11b activation-specific epitope [AE], in a human whole blood assay. All together, these data supported the progression of 99 toward next phases, becoming the first FFA2 antagonist to reach the clinic.

Substituted β-alanine derivatives as cell adhesion inhibitors

β-Alanine derivatives of Formula I are antagonists of VLA-4 and/or α4β7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of asthma, allergies, inflammation, multiple sclerosis, and other inflammatory and autoimmune disorders.