34271-50-6

Usage

InChI:InChI=1/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3/t12-/m1/s1

Upstream product

• 115787-52-5 5-(2-tert-Butylamino-acetyl)-2-hydroxy-benzaldehyde 
• 115787-50-3 5-(2-bromoacetyl)-2-hydroxybenzaldehyde 
• 115787-57-0 2-Chloro-1-<3-<<(1,1-dimethylethyl)imino>methyl>-4-hydroxyphenyl>ethanone 
• 115787-56-9 2-Bromo-1-<3-<<(1,1-dimethylethyl)imino>methyl>-4-hydroxyphenyl>ethanone 
• 54208-72-9 2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol 
• 115787-53-6 5-<<(1,1-Dimethylethyl)amino>acetyl>-2-hydroxybenzaldehyde hydrochloride 
• 90-02-8 salicylaldehyde 
• 24085-03-8 α-[(benzyl-tert-butylamino)methyl]-m-xylene-4,α,α'-triol 
• 324000-05-7 2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol 
• 18559-94-9 Salbutamol 
• 24085-06-1 4'-acetoxy-3'-(acetoxymethyl)acetophenone 
• 99-93-4 4-Hydroxyacetophenone 
• 75-64-9 tert-butylamine 
• 67-56-1 methanol 

Downstream Products

• 54208-72-9 2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol 
• 324000-05-7 2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol 
• 102015-18-9 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-nitrophenol 
• 35459-13-3 (-)-(R)-salbutamol acetate 
• 62084-23-5 (+/-)-albuterol tri(trimethylsilyl)ether 

Relevant academic research and scientific papers

Effect of additives on eremomycin sorbent selectivity in separation of salbutamol enantiomers using supercritical fluid chromatography

A regime is found in which chiral stationary phase based on macrocyclic glycopeptide eremomycin allows separation of salbutamol sulfate enantiomers in supercritical fluid chromatography. Enantioseparation occurs only when two dynamic modifiers are used simultaneously: isopropylamin + trifluoroacetic acid or isopropylamin + ammonium acetate. Amine molar concentration in mobile phase has to be higher than acid molar concentration, otherwise enantiomers coelute. We suppose that with amine excess a mechanism of enantiorecognition is realized which involves ionic sorbent-sorbate interactions. Such mechanism is well-known for glycopeptide chiral selectors in liquid chromatography, but for supercritical fluid chromatography it is reported for the first time.

Preparation method of salbutamol sulfate

The invention provides a preparation method of salbutamol sulfate, and relates to the technical field of chemical synthesis. The preparation method of salbutamol sulfate comprises the following steps: (a) carrying out reaction on salicylic acid and a tert-butyl amino acetyl halogenating reagent under the action of a chlorinating agent to generate an intermediate 1; (b) reacting the intermediate 1 under the action of Lewis acid to generate an intermediate 2; (c) reacting the intermediate 2 under the action of an acid reagent to generate an intermediate 3; (d) reacting the intermediate 3 with a reducing agent under the action of a catalyst to generate salbutamol; and (e) reacting salbutamol with sulfuric acid to generate salbutamol sulfate. The raw materials are simple and easy to obtain, the reaction condition is mild, the reaction operation is simple, the reaction process is easier to control, and the safety coefficient is high; used raw materials, solvents and the like are environment-friendly; and the yield and purity of salbutamol sulfate are high, and a process route capable of industrially producing a product with higher quality is provided.

Preparation method of racemic salbutamol

The invention discloses a preparation method of racemic salbutamol. The method comprises the following steps: taking 5-bromosalicylaldehyde as a raw material, carrying out reduction reaction on the 5-bromosalicylaldehyde and sodium borohydride to obtain an intermediate I; carrying out alkylation reaction on the intermediate I, sodium hydride and benzyl halide to obtain an intermediate II; carryingout cross-coupling reaction on the intermediate II and vinyl potassium trifluoroborate to obtain an intermediate III; carrying out addition reaction on the intermediate III and N-bromo succinimide toobtain an intermediate IV; carrying out alkylation reaction on the intermediate IV and tert-butylamine to obtain an intermediate V; and carrying out deprotection reaction on the intermediate V in a hydrogen atmosphere to obtain the racemic salbutamol. The 5-bromosalicylaldehyde is used as a reaction raw material for the first time to reduce the production cost, and bromine atoms are introduced, so that functional groups can be directionally introduced to the 5th site by the reaction, and the selectivity and yield of the reaction are improved; no high-risk highly toxic reagent is involved; andthe Suzuki-Miyaura cross-coupling reaction is applied to synthesis of salbutamol for the first time, and a catalytic amount of palladium catalyst is used, so that efficient introduction of double bonds on an aromatic ring can be realized, and the cost is reduced while the reaction yield is increased.

A chromatography-free synthesis of racemic salbutamol hemisulfate

Our efforts to achieve an efficient synthesis of racemic salbutamol hemisulfate are described. The selected chemical route starts from commodity chemicals and allows the generation of salbutamol hemisulfate in 5 steps and 44% overall yield without any purification by column chromatography. The reaction sequence has been optimized to provide the title compound using robust procedures. Emphasis on reproducibility and experimental simplicity drove the work described herein.

Preparation method of salbutamol sulfate intermediate

The invention provides a preparation method of a salbutamol sulfate intermediate. Salbutamol is a beta receptor stimulant; a current preparation technology of the salbutamol mainly takes an original research technology as a main part; the original research technology takes p-hydroxyacetophenone as a starting material and the salbutamol is prepared through chloromethylation, esterification, bromination, amination, hydrolysis and reduction. An existing synthesis method of the salbutamol sulfate intermediate is used for synthesizing through a plurality of steps and is complicated to operate; theloss of products in a preparation process is great and the technological time is relatively long. The preparation method of the salbutamol sulfate intermediate, provided by the invention, comprises the following steps: reducing carbonyl of a compound I under the action of a reducing agent to obtain a compound II; then adding a debenzylation reagent and carrying out debenzylation reaction to obtainthe salbutamol sulfate intermediate III. According to the preparation method, the salbutamol sulfate intermediate III is prepared from the compound I by adopting a 'one-pot method'; operation steps are reduced, the reaction time is shortened and the reaction yield is improved.

Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography

In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with open-tubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L9(34). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5?μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77?mmol·m?2. The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.

Preparation method of free racemic albuterol

The invention discloses a preparation method of free racemic albuterol. The preparation method comprises the following steps: with methyl salicylate as a raw material, successively carrying out Friedel-Crafts acylation and oxidation, carrying out condensation and borate reduction in pure water with a 'one-pot' method, carrying out ester group reduction and acetonylidene protection of crude albuterol with a 'one-pot' method, and carrying out deprotection and purification to obtain the free racemic albuterol. The preparation method has the advantages of high labor efficiency, low reaction reagent cost and high yield.

Method for preparing salbutamol

The invention provides a preparation method of an intermediate salbutamol of salbutamol sulfate. The method comprises the following steps: (1) preparing acidified gel type strongly acidic cation exchange resin or macroporous type strongly acidic cation exchange resin through hydrochloric acid elution; (2) carrying out propylidene protection group removal on a compound shown as a formula I by utilizing the acidified acidic cation exchange resin; then filtering to remove the acidic cation exchange resin, so as to obtain filtrate containing a compound salbutamol shown as a formula II; (3) regulating the pH (Potential of Hydrogen) value of the filtrate to be 9 to 10 and filtering to separate out a solid, so as to obtain the salbutamol. According to the preparation method provided by the invention, the propylidene protection group removal is carried out on the strongly acidic cation exchange resin; the method is simple to operate, short in reaction time and high in yield; strong acid is notused so that corrosion, caused by the strong acid, to equipment is avoided and harms, caused by the strong acid, to health of operators are reduced. Furthermore, the acidic cation exchange resin canbe repeatedly utilized and the production cost can be greatly reduced.

Resorcinol-, catechol- and saligenin-based bronchodilating β2-agonists as inhibitors of human cholinesterase activity

We investigated the influence of bronchodilating β2-agonists on the activity of human acetylcholinesterase (AChE) and usual, atypical and fluoride-resistant butyrylcholinesterase (BChE). We determined the inhibition potency of racemate and enantiomers of fenoterol as a resorcinol derivative, isoetharine and epinephrine as catechol derivatives and salbutamol and salmeterol as saligenin derivatives. All of the tested compounds reversibly inhibited cholinesterases with Ki constants ranging from 9.4 μM to 6.4 mM and had the highest inhibition potency towards usual BChE, but generally none of the cholinesterases displayed any stereoselectivity. Kinetic and docking results revealed that the inhibition potency of the studied compounds could be related to the size of the hydroxyaminoethyl chain on the benzene ring. The additional π–π interaction of salmeterol’s benzene ring and Trp286 and hydrogen bond with His447 probably enhanced inhibition by salmeterol which was singled out as the most potent inhibitor of all the cholinesterases.

Comparison of three S-β-CDs with different degrees of substitution for the chiral separation of 12 drugs in capillary electrophoresis

Three kinds of sulfated β-cyclodextrin (S-β-CD), including a single isomer, heptakis-6-sulfato-β-cyclodextrin (HS-β-CD), degree of substitution (DS) of 7, which was synthesized in our laboratory and another two commercialized randomly substituted mixtures, a sulfated β-cyclodextrin with DS of 7 to 11, as well as a highly sulfated-β-cyclodextrin with DS of 12 to 15, were used for the enantioresolution of 12 drugs (the β-blockers, phenethylamines, and anticholinergic agents) in capillary electrophoresis. The enantioseparation under varying concentrations of S-β-CD and background electrolyte pH were systematically investigated and compared. Based on the experimental results, the effect of the nature of S-β-CD and analyte structure on the enantioseparation is discussed.