104141-93-7

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 75-65-0 tert-butyl alcohol 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 171364-80-0 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 201230-82-2 carbon monoxide 
• 619-45-4 4-methoxycarbonyl aniline 
• 1679-64-7 Monomethyl terephthalate 
• 20576-82-3 terephthalic acid mono-tert-butyl ester 
• 143707-77-1 4-(tert-butoxycarbonyl)benzoyl chloride 
• 67-56-1 methanol 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 

Downstream Products

• 1415902-27-0 C₁₁H₁₁FO₆S 
• 1415902-28-1 C₁₅H₁₄FNO₈S 
• 1415902-30-5 C₁₅H₁₉⁽¹⁸⁾FO₆S 
• 1415902-31-6 C₁₁H₁₁⁽¹⁸⁾FO₆S 
• 1415902-29-2 C₁₅H₁₄⁽¹⁸⁾FNO₈S 
• 1415902-26-9 C₁₅H₁₉FO₆S 
• 1415902-25-8 sultone-benzoic acid tert-butyl ester 
• 1679-64-7 Monomethyl terephthalate 

Relevant academic research and scientific papers

Thieme Chemistry Journals Awardees - Where Are They Now? Bis(2-pyridyl)amides as Readily Cleavable Amides under Catalytic, Neutral, and Room-Temperature Conditions

Mild solvolytic cleavage of bis(2-pyridyl)amide under neutral and room-temperature conditions is described. The inherently stable amide was readily activated by catalytic amounts of metal cations to react with alcohols. Based on X-ray crystallographic analysis, the primary driving force was considered to be amide distortion induced by the metal coordination of two pyridyl groups in a bidentate fashion without affecting the amide functionality. The compatibility of the acid/base-sensitive functionalities and the absence of racemization during solvolysis highlight the mildness of the present protocol.

Preparation of tert-butyl esters via Pd-catalyzed tert-butoxycarbonylation of (hetero)aryl boronic acid derivatives

A novel protocol to synthesize tert-butyl esters from boronic acids or boronic acid pinacol esters and di-t-butyl dicarbonate has been successfully achieved. The cross-coupling reactions can produce up to 94% yields by using palladium acetate and triphenylphosphine as catalyst system, dioxane as a solvent. Moreover, a wide range of substrates including benzenes, pyridines, and quinolines boronic acids or boronic acid pinacol esters can fit with this system as well.

C-C Bond Cleavage of Unactivated 2-Acylimidazoles

2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

Metal-free radical aromatic carbonylations mediated by weak bases

We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism.

Reagent-free continuous thermal tert-butyl ester deprotection

Continuous processing enables the use of non-standard reaction conditions such as high temperatures and pressures while in the liquid phase. This expands the chemist's toolbox and can enable previously unthinkable chemistry to proceed with ease. For a series of amphoteric amino acid derivatives, we have demonstrated the ability to hydrolyze the tert-butyl ester functionality in protic solvent systems. Using a continuous plug flow reactor at 120–240 °C and 15–40 min reaction times, no pH modification or additional reagents are needed to achieve the desired transformation. The method was then expanded to encompass a variety of more challenging substrates to test selectivity and racemization potential. The acid products were generally isolated as crystalline solids by simple solvent exchange after the deprotection reaction in good to high yield and purity.

A larene/ fragrant mixedsurrounds uncle butanol method for preparing ester compounds

The invention discloses a preparation method of an aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound. The preparation method of the aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound comprises the following steps of: firstly, under stirring condition, adding aromatic heterocycle borate compound or aromatic ring boric acid compound and di-tert-butyl dicarbonate ester into a solvent, and then adding a palladium catalyst and a ligand, so that a mixture A is obtained; secondly, heating the mixture A for carrying out reaction, and then cooling to room temperature, so that a mixture B is obtained; thirdly, diluting the mixture B with ethyl acetate, then filtering the diluted mixture B with diatomite, collecting filtrate, concentrating, and carrying out spin drying, so that the aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound is obtained. The preparation method of the aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound has the advantages that alkoxycarbonylation reaction on an aromatic heterocycle borate compound or aromatic ring boric acid compound is realized, and the aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound is directly generated; raw materials are non-toxic, inexpensive and available; a catalytic system is low in cost and has good stability and broad applicability; reaction conditions are mild, safety is high, and control is easy; a technology is simple, operation is easy, environmental friendliness is realized, and specificity is strong, so that the preparation method of the aromatic ring/aromatic heterocycle tert-butyl alcohol ester compound is applicable to industrialized production.

NEW NUCLEOPHILE-REACTIVE SULFONATED COMPOUNDS FOR THE (RADIO)LABELLING OF (BIO)MOLECULES; PRECURSORS AND CONJUGATES THEREOF

The invention relates to nucleophile-reactive sulfonated compounds used as precursors to (radio)labelled (bio)molecules suitable mainly for medical applications. The aim of the invention is to provide novel prosthetic compounds or groups, the synthesis of which is straightforward, easy and automatable, enabling access to economical and effective, (radio)labelled, complex and fragile - especially water-soluble and more especially amine-containing- (bio)molecules. The aim is achieved by the invention, which involves precursors and compounds of respective formulae (Ip), (I). Said nucleophile-reactive sulfonated compounds are produced by pre-introduction of a nucleophilic compound R*, e.g. Fluorine- 18, through an unusal nucleophile-induced ring-opening reaction of the sultone (e.g. 1,3-propanesultone) moiety of the precursor. The invention also relates to the methods for producing the abovementioned precursors and compounds, as well as for the conjugation of these compounds with (bio)molecules, and to the drugs obtained through this method.

A novel sulfonated prosthetic group for [18F]-radiolabelling and imparting water solubility of biomolecules and cyanine fluorophores

Synthesis and some applications of a novel [18F]-fluorinated prosthetic group based on the promising sultone radiochemistry and suitable for the labelling of amine-containing (bio)chemical compounds are described. The combined sequential use of two easy and efficient conjugation reactions namely the fluoride ring-opening of a 1,3-propanesultone moiety and the aminolysis of an N-hydroxysuccinimidyl ester is the key component of this original radiolabelling strategy. The mild reaction conditions and the release of a free sulfonic acid moiety as a result of the [18F]-induced sultone ring-opening reaction, both make this [18F]-conjugation method suitable for the radiofluorination of fragile and hydrophobic biomolecules and fluorophores, particularly by making the separation of the targeted [ 18F]-tagged sulfonated compound from its starting precursor easier and thus faster. The ability of this unusual prosthetic group to readily introduce the radioisotope within complex (bio)molecular architectures has been demonstrated by (1) the preparation of the first [18F]-labelled cyanine 5.5 (Cy 5.5) dye, a suitable precursor for the construction of hybrid positron emission tomography/near-infrared fluorescence (PET/NIRF) imaging probes and (2) the radiolabelling of a biologically relevant peptide bearing a single lysine residue. The Royal Society of Chemistry 2013.

Esters as acylating reagent in a Friedel-Crafts reaction: Indium tribromide catalyzed acylation of arenes using dimethylchlorosilane

(Chemical Equation Presented) The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me2 is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis of the indanone intermediate 11 of salviasperanol from ester 10.

A Simple, Powerful, and Efficient Method for Transesterification

Aromatic and α,β-unsaturated methyl esters undergo efficient transesterification at ambient temperature or below with primary, secondary, or (particularly) tertiary alcohols in the presence of butyl-lithium in tetrahydrofuran solution.