610791-05-4

Basic information

• Product Name: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER
• Synonyms: TERT-BUTYL METHYL AZETIDINE-1,3-DICARBOXYLATE;1-BOC-AZETIDINE-3-CARBOXYLIC ACID METHYL ESTER;AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER;Methyl 1-Boc-azetidine-3-carboxylate;1-tert-butyl 3-methyl azetidine-1,3-dicarboxylate;N-Boc-3-azetidine carboxylic acid methyl ester;Methyl 1-Boc-azetidine-3-...;Methyl azetidine-3-carboxylate, N-BOC protected
• CAS NO: 610791-05-4
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.25
• Product Categories: pharmacetical
• Mol File: 610791-05-4.mol

Chemical Properties

• Boiling Point: 269°C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.072 g/mL at 25 °C
• Vapor Pressure: 0.00743mmHg at 25°C
• Refractive Index: n20/D1.452
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -2.97±0.40(Predicted)
• CAS DataBase Reference: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(610791-05-4)
• EPA Substance Registry System: AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER(610791-05-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 610791-05-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER is used as a building block for the synthesis of azaspiro[3.4]octanes, as developed in the Carreira group. Its unique structure and reactivity make it a valuable precursor in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER can be used as a starting material for the development of novel drugs. Its ability to be functionalized via enolization at the 3-position in the presence of LDA (lithium diisopropylamide) allows for the creation of diverse chemical entities with potential therapeutic applications.
Used in Research and Development:
AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER is also utilized in research and development settings, where it can be employed to study the properties and reactivity of various chemical compounds. Its functionalization capabilities make it an attractive candidate for exploring new reaction pathways and developing innovative synthetic methods.

InChI:InChI=1/C10H17NO4/c1-10(2,3)15-9(13)11-5-7(6-11)8(12)14-4/h7H,5-6H2,1-4H3

Upstream product

• 100202-39-9 methyl 3-azetidinecarboxylate hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 142253-55-2 1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 53871-06-0 1-(diphenylmethyl)-3-methoxycarbonylazetidine 
• 343238-58-4 methyl azetidine-3-carboxylate 

Downstream Products

• 142253-56-3 3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 1340481-93-7 C₁₁H₁₉NO₃S 
• 1340481-94-8 C₁₁H₁₉NO₅S 
• 1340481-92-6 C₁₉H₂₇NO₅S 
• 1340481-90-4 C₁₁H₁₉NO₅S 
• 1340481-91-5 C₁₁H₁₇NO₅S 
• 1340481-87-9 C₁₈H₂₇NO₄S 
• 1257293-79-0 tert-butyl 3-(2-hydroxypropan-2-yl)azetidine-1-carboxylate 
• 1449329-46-7 3-[(2S,4R)-4-(2-chloro-4-methoxy-benzenesulfonyl)-2-(1-cyano-cyclopropylcarbamoyl)-pyrrolidine-1-carbonyl]-3-(5-chloro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester 
• 1346674-11-0 tert-butyl 3-(3-amino-1H-pyrazol-5-yl)azetidine-1-carboxylate 
• 887594-13-0 tert-butyl 3-(2-cyanoacetyl)azetidine-1-carboxylate 
• 177947-96-5 tert-butyl 3-formylazetidine-1-carboxylate 
• 1443983-85-4 tert-butyl 3-(fluoromethyl)azetidine-1-carboxylate 
• 142253-57-4 3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Facile synthesis of 2-azaspiro[3.4]octane

Our annulation strategy utilized for the synthesis of 2-azaspiro[3.4]octane is explained. Three successful routes for the synthesis were developed. One of the approaches involved annulation of the cyclopentane ring and the remaining two approaches involved annulation of the four membered ring. All three approaches employ readily available starting materials with conventional chemical transformations and minimal chromatographic purifications to afford the title compound. The merits and limitations of the three approaches are also discussed.

TARGETING COMPOUNDS

The disclosure provides, at least in part, liver, intestine and/or kidney-targeting compounds and their use in treating liver, intestine and/or kidney disorders, such as non-alcoholic steatohepatitis, alcoholic steatohepatitis, hepatocellular carcinoma, liver cirrhosis, and hepatitis B; and/or chronic kidney disease, glomerular disease such as IGA nephropathy, lupus nephritis, or polycystic kidney disease. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

PROCESS FOR THE PREPARATION OF 2-(3-(FLUOROMETHYL)AZETIDIN-1-YL)ETHAN-1-OL

Methods of making 2-(3-(fluoromethyl)azetidin-1-yl)ethan-1-ol 9, an intermediate useful for the synthesis of estrogen receptor modulating compounds are described.

Polysubstituted-indazole compounds and application of same as IDO inhibitors

The invention discloses polysubstituted-indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application of the compounds as IDO inhibitors. The compounds provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections related to cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.

Preparation method of 2-(1-(tertbutyloxycarbonyl)azacyclobutyl-3-yl)cyclopropanecarboxylic acid

The invention relates to a preparation method of 2-(1-(tertbutyloxycarbonyl)azacyclobutyl-3-yl)cyclopropanecarboxylic acid. The preparation method solves the problem that the existing appropriate 2-(1-(tertbutyloxycarbonyl)azacyclobutyl-3-yl)cyclopropanecarboxylic acid industrial synthesis method does not exist. The preparation method comprises that 1, a compound 1 and iodomethane undergo a reaction under alkaline conditions to produce a compound 2, 2, the compound 2 is treated by sodium borohydride to form a compound 3, 3, the compound 3 is oxidized by Dess-Martin periodinane to form a compound 4, 4, the compound 4 and a compound 5 undergo a reaction to produce a compound 6, 5, the compound 6 and trimethylsulfoxonium iodide undergo a reaction to produce a compound 7, and 6, the compound 7 is hydrolyzed under alkaline conditions to form an end product compound 8. The reaction equation is shown in the following description. The 2-(1-(tertbutyloxycarbonyl)azacyclobutyl-3-yl)cyclopropanecarboxylic acid is a useful intermediate or product for synthesis of many drugs.

3-SUBSTITUTED PYRAZOLES AND USE AS DLK INHIBITORS

The present invention provides for compounds of Formula (I) and various embodiments thereof, and compositions comprising compounds of Formula (I) and various embodiments thereof. (I) In compounds of Formula I, the groups R1, R2, R3, R4, R5, R6 and R7 have the meaning as described herein. The present invention also provides for methods of using compounds of Formula I and compositions comprising compounds of Formula (I) as DLK inhibitors and for treating neurodegeneration diseases and disorders.

NOVEL COMPOUNDS AND THEIR USE IN THERAPY

The invention provides compounds which inhibit N-myristoyltransferase and are selective for protozoal N-myristoyltransferase and, consequently suitable to treat microbial infections, including viral and fungal infections, and protozoan infections such as malaria, leishmaniasis and sleeping sickness.

FUSED IMIDAZOLE DERIVATIVES USEFUL AS IDO INHIBITORS

Presently provided are IDO inhibitors and pharmaceutical compositions thereof, useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated inimunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.