tert-Butyl 3-oxoazetidine-1-carboxylate Chemical Properties

Melting point:

47-51 °C

Boiling point:

251.3±33.0 °C(Predicted)

Density 

1.174±0.06 g/cm3(Predicted)

Flash point:

102 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Dichloromethane (Slightly)

pka

-1.99±0.20(Predicted)

form 

Crystalline Powder

color 

White to off-white

Sensitive 

Moisture Sensitive/Stench

InChI

InChI=1S/C8H13NO3/c1-8(2,3)12-7(11)9-4-6(10)5-9/h4-5H2,1-3H3

InChIKey

VMKIXWAFFVLJCK-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(=O)C1

CAS DataBase Reference

398489-26-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

UN 3335

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

tert-Butyl 3-oxoazetidine-1-carboxylate Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

1-Boc-3-azetidinone can be used for the preparation of antibacterial aminoglycoside analogs.

Uses

tert-Butyl 3-oxoazetidine-1-carboxylate(1-Boc-3-azetidinone) is a currently common organic intermediate. It is a key intermediate for preparing various medicaments. It can be used for preparing Janus kinase 3(JAKS), which is a useful target for immunosuppression and transplant rejection, and can be used for treating inflammatory disorders, autoimmune disorders, cancer and other diseases; also useful in the preparation of a second class of HCV protease inhibitors useful in the treatment of HCV genotype 1 infection; can also be used for preparing novel aminoglycoside compounds with antibacterial activity; bicyclic himbacine (himbacine) derivatives can be prepared which are useful as antagonists of the protease activated receptor-1 (PAR-1) and are predicted to be cannabis (CB2) receptor inhibitors, useful for the treatment of secondary prevention of Acute Coronary Syndrome (ACS), myocardial infarction or thrombotic stroke or peripheral arterial disease; bicyclic azacyclobenzylamine derivatives, such as pyridopyrimidines, can be prepared that modulate the activity of phospho-inositol 3-kinase (P13K) and are useful in the treatment of diseases associated with P13K, including, for example, inflammatory disorders, immune-based disorders, cancer, and other diseases.

General Description

tert-Butyl 3-oxoazetidine-1-carboxylate is moisture sensitive and incompatible with oxidizing agents. This chemical can cause skin irritation and severe eye irritation.

Synthesis

The traditional preparation method of tert-Butyl 3-oxoazetidine-1-carboxylate is mainly to oxidize the hydroxyl on an aza ring into ketone. For example: 3-azetidinium alkoxide, di-tert-butyl dicarbonate and sodium bicarbonate in dioxane: stirring the mixture of water for 15 hours to obtain 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethylethyl ester; dissolving 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethyl ethyl ester in ethanedioyl chloride and dichloromethane, adding DMSO and triethylamine, stirring at room temperature for 15 hours to obtain tert-Butyl 3-oxoazetidine-1-carboxylate.

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