77629-96-0

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL 2,4-DIBROMOBUTYRATE is used as a building block for the synthesis of various pharmaceutical compounds, particularly azetidine-2-carboxylates. These compounds are important in the development of drugs that target specific biological pathways and have potential therapeutic applications.
Used in Chemical Synthesis:
TERT-BUTYL 2,4-DIBROMOBUTYRATE is used as a reagent in chemical synthesis, where it can react with primary amines to yield azetidine-2-carboxylates. This reaction is significant in the production of various chemical compounds that have a wide range of applications, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C8H14Br2O2/c1-8(2,3)12-7(11)6(10)4-5-9/h6H,4-5H2,1-3H3

Upstream product

• 96-48-0 4-butanolide 
• 115-11-7 isobutene 
• 63164-16-9 2,4-dibromo-butyric acid 
• 75-65-0 tert-butyl alcohol 
• 82820-87-9 2,4-dibromobutanoyl chloride 

Downstream Products

• 65219-09-2 N-(2,4,6-Trimethoxybenzyl)-2-(carbo-tert-butoxy)azetidine 
• 72089-77-1 N-Cyclohexyl-2-(carbo-tert-butoxy)azetidine 
• 77647-99-5 N-(2-Phenylethyl)-2-(carbo-tert-butoxy)azetidine 
• 1398752-13-0 3-(1,1-dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate 
• 1353161-08-6 tert-butyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate 
• 65219-12-7 2-[1-tert-Butoxy-1-(tert-butyl-dimethyl-silanyloxy)-meth-(Z)-ylidene]-1-(2,4,6-trimethoxy-benzyl)-azetidine 
• 138883-20-2 (+/-)-tert-butyl 1,4-diazepane-5-carboxylate 
• 77647-98-4 tert-butyl N-benzylazetidine-2-carboxylate 
• 345317-99-9 N-(α-Carbethoxy-p-methoxybenzyl)-2-(carbo-tert-butoxy)azetidine 
• 71725-03-6 Ethyl α--2-(carbo-tert-butoxy)-1-azetidineacetate 

Relevant academic research and scientific papers

N-(PYRIDIN-2-YLSULFONYL)CYCLOPROPANECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF A CFTR MEDIATED DISEASE

The invention relates to heterocyclic compounds of the formula (I), in which all of the variables are as defined in the specification; capable of modulating the activity of CFTR. The invention further provides a method for manufacturing compounds of the invention, and its therapeutic uses. The invention further provides methods to their preparation, to their medical use, in particular to their use in the treatment and management of diseases or disorders including Cystic fibrosis and related disorders.

Base-promoted diastereoselective α-alkylation of borane: N -((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes

The base-promoted α-alkylation of N-((S)-1-phenylethyl)azetidine-2-carboxylic acid esters 1 was investigated. The use of diastereomerically pure borane complexes 3 as substrates, which are easily prepared from 1, dramatically improved the yields and diastereoselectivities of α-alkylated products 2. For example, the treatment of tert-butyl ester (1S,2S,1′S)-3a with 2.4 equivalents of lithium bis(trimethysilyl)amide (LiHMDS) at 0 °C followed by 2.6 equivalents of benzyl bromide afforded α-benzylated (2S,1′S)-2aa in 90% yield as almost a single diastereomer. Our method enables the production of optically active α-substituted azetidine-2-carboxylic acid esters starting from commercially available (S)-1-phenylethylamine, which is one of the least expensive chiral compounds.

Synthesis of Substituted Cyclopropanecarboxylates via Room Temperature Palladium-Catalyzed α-Arylation of Reformatsky Reagents

The room temperature palladium-catalyzed cross-coupling of aromatic and heteroaromatic halides with Reformatsky reagents derived from 1-bromocyclopropanecarboxylates provides an exceptionally mild method for enolate α-arylation. The method is tolerant of a wide range of functionalities and dramatically shortens many of the existing routes to access widely used 1,1-disubstituted cyclopropanecarboxylate derivatives.

Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations

The base-induced Sommelet–Hauser (S–H) rearrangement of azetidine-2-carboxylic acid ester-derived ammonium salts into 2-aryl-substituted derivatives was demonstrated. The ring-strain of four-membered N-heterocycles enables efficient generation of the desired ylide intermediate and enhances the rate of the S–H rearrangement. The asymmetric version of the rearrangement was characterized by excellent levels of successive chirality transmissions. The regio- and stereo-controlled nucleophilic ring opening of the rearrangement products produced quaternary α-aryl amino acid esters with excellent enantiopurities.

Peptide deformylase inhibitors

The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhibition of bacterial peptide deformylase (PDF) activity.

PEPTIDE DEFORMYLASE INHIBITORS

The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhi-bition of bacterial peptide deformylase (PDF) activity