86073-42-9

Usage

Uses

Used in Pain Management Applications:
Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]is used as an analgesic agent for the treatment of moderate to severe acute and chronic pain. Its dual mechanism of action, which includes mu-opioid receptor agonism and noradrenaline reuptake inhibition, offers effective pain relief with a reduced risk of gastrointestinal side effects compared to traditional opioids.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]is utilized as a key ingredient in various formulations, such as immediate-release and extended-release tablets. Its prescription is closely monitored due to its potential for dependence and abuse, ensuring that patients receive the appropriate dosage and supervision for safe and effective pain management.
Common side effects associated with the use of Acetamide, N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]may include dizziness, nausea, constipation, and drowsiness. However, its innovative approach to pain relief makes it a valuable asset in the management of various types of pain, offering patients an alternative to traditional opioid medications.

Upstream product

• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 141-78-6 ethyl acetate 
• 140-67-0 Estragole 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 108-24-7 acetic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 69390-41-6 (E)-N-(1-(4-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 37629-51-9 1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene 

Downstream Products

• 112101-74-3 (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide 
• 408497-91-6 N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 
• 245759-61-9 (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 299964-43-5 (R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 73573-87-2 (R,R)-formoterol 
• 58993-79-6 (R)-(-)-p-methoxyamphetamine 

Relevant academic research and scientific papers

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).

Amine dehydrogenases: Efficient biocatalysts for the reductive amination of carbonyl compounds

Amines constitute the major targets for the production of a plethora of chemical compounds that have applications in the pharmaceutical, agrochemical and bulk chemical industries. However, the asymmetric synthesis of α-chiral amines with elevated catalytic efficiency and atom economy is still a very challenging synthetic problem. Here, we investigated the biocatalytic reductive amination of carbonyl compounds employing a rising class of enzymes for amine synthesis: amine dehydrogenases (AmDHs). The three AmDHs from this study-operating in tandem with a formate dehydrogenase from Candida boidinii (Cb-FDH) for the recycling of the nicotinamide coenzyme-performed the efficient amination of a range of diverse aromatic and aliphatic ketones and aldehydes with up to quantitative conversion and elevated turnover numbers (TONs). Moreover, the reductive amination of prochiral ketones proceeded with perfect stereoselectivity, always affording the (R)-configured amines with more than 99% enantiomeric excess. The most suitable amine dehydrogenase, the optimised catalyst loading and the required reaction time were determined for each substrate. The biocatalytic reductive amination with this dual-enzyme system (AmDH-Cb-FDH) possesses elevated atom efficiency as it utilizes the ammonium formate buffer as the source of both nitrogen and reducing equivalents. Inorganic carbonate is the sole by-product.

Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation

WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number). Copyright

Practical syntheses of N-acetyl (E)-β-arylenamides

A facile and practical method for the preparation of (E)-β- arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key chiral intermediate of tamsulosin by asymmetric hydrogenation. Georg Thieme Verlag Stuttgart . New York.

Stereoselectivity of four (R)-selective transaminases for the asymmetric amination of ketones

Four (R)-ω-transaminases originating from Hyphomonas neptunium (HN-ωTA), Aspergillus terreus (AT-ωTA) and Arthrobacter sp. (ArR-ωTA), as well as an evolved transaminase (ArRmut11-ωTA) were successfully employed for the amination of prochiral ketones leading to optically pure (R)-amines. The first three transaminases displayed perfect stereoselectivity for the amination of all substrates tested (ee >99%). Furthermore, the transaminase AT-ωTA led in most cases to better conversion than ArR-ωTA and HN-ωTA using D-alanine as amine donor. α-Tetralone, which was the only substrate not accepted by HN-ωTA, ArR-ωTA, and AT-ωTA, was successfully transformed with perfect enantioselectivity (ee >99%) into the corresponding optically pure amine employing the variant ArRmut11-ωTA. Copyright

Process for preparation of tamsulosin and its aralkylamine derivatives

The present invention discloses a new process for the synthesis of tamsulosin and its aralkylamine derivatives, especially (R)-(?)-5-{2-[2-(2-alkoxyphenoxy)ethylamino]propyl}-2-alkoxybenzenesulfonamides having the following formula 1 (where R1 and R2 represent C1-C4 alkyl groups) and their hydrochloride thereof, and other various pharmaceutical used salts. Tamsulosin hydrochloride (R1=Et, R2=Me, in its hydrochloride salt form) is an antagonist of α-A adrenoceptors in the prostate. Tamsulosin?HCl occurs as white crystals, which melt with decomposition at approximately 230° C. It is sparingly soluble in water and in methanol, slightly soluble in glacial acetic acid and in ethanol, and practically insoluble in ether.

Process for preparation of tamsulosin and its derivatives

The present invention discloses a new process for the synthesis of tamsulosin derivatives of formula 1 (where R 1 and R 2 represent C 1 -C 4 alkyl groups) and their hydrochlorides and other pharmaceutically acceptable salts, comprising reacting the hydrochloride of sulphonamide 2 (where R represents C 1 -C 4 alkyl) with the ether compound 21 (where R' represents C 1 -C 4 alkyl and R" represents MeC 6 H 4 SO 2 or MeSO 2 ).

CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines

Some pharmacologically active amines such as amphetamine, the isomeric o-, m- and p-methoxyamphetamines, 4-phenylbutan-2-amine and mexiletine, as well as their corresponding acetamides, have been prepared in high yields and with very high enantiomeric excesses. The method consists of the Candida antarctica lipase B (CAL-B)-mediated enantioselective acetylation of racemic amines using ethyl acetate as solvent and acyl donor. The enzyme follows Kazlauskas' rule with all amines, (R)-amides being obtained as the major enantiomer in all cases. From the conversion values measured for both enantiomers, it can be deduced that the size of the substituents attached to the stereocenter is responsible for the enantioselectivity and rate of some of these reactions.

An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

The potent β2-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. Copyright (C) 2000 Elsevier Science Ltd.

Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them

A novel process is provided for the preparation of optical isomers of certain sulfamoyl-substituted phenethylamine derivatives which exhibit α-adrenergic blocking agents which can be used for various treatments such as for the treatment of congestive heart failure.