81601-93-6

Upstream product

• 67-56-1 methanol 
• 22071-15-4 ketoprofen 
• 89539-11-7 2-(3-(α-hydroxybenzyl)phenyl)propanal dimethyl acetal 
• 67333-36-2 methyl α-methylthio-α-(m-benzoylphenyl)-propionate 
• 5188-07-8 sodium thiomethoxide 
• 118633-39-9 Benzoesaeure--anhydrid 
• 142569-76-4 methyl 2-(2-iodophenyl)propionate 
• 201230-82-2 carbon monoxide 
• 80622-53-3 methyl 2-(3-bromophenyl)propanoate 
• 98-80-6 phenylboronic acid 
• 119-61-9 benzophenone 
• 5445-17-0 Methyl 2-bromopropionate 
• 1016-77-9 3-bromobenzophenone 
• 56105-81-8 R-ketoprofen 

Downstream Products

• 22161-81-5 S-ketoprofen 
• 56105-81-8 R-ketoprofen 
• 138682-99-2 methyl 2-(3-(hydroxy-phenyl-methyl)-phenyl)-propionate 
• 856893-03-3 2-(3-benzoylphenyl)-3-methoxy-2-methylpropionic acid methyl ester 
• 321879-84-9 methyl 2-[3-(2-phenyl-1,3-dioxolan-2-yl)phenyl]propionate 
• 461382-72-9 methyl 2,2'-(3-benzoylphenyl)-methylhexanoate 
• 118591-56-3 methyl 2-[3-(1-phenylethyl)phenyl]propanoate 
• 1073126-84-7 2-(3-benzoylphenyl)propanehydrazide 
• 22071-15-4 ketoprofen 
• 1260498-36-9 methyl 2-(3-benzoylphenyl)-2-methylpentanoate 
• 1262801-32-0 C₁₇H₁₄N₂O₂S 
• 1262801-26-2 3-[2-{5-(1-(3-benzoylphenyl)ethyl)-1,3,4-oxadiazol-2-ylthio}acetyl]-2H-chromen-2-one 

Relevant academic research and scientific papers

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Preparation method of carboxylic ester compound

The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.

CHEMOSELECTIVE METHYLENE HYDROXYLATION IN AROMATIC MOLECULES

A chemoselective and reactive Mn(CF3-PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

Hydroarylation of Alkenes by Protonation/Friedel-Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters

Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Br?nsted bases and protonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel-Crafts hydroarylation which procee

Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides

A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.

Ruthenium(II)-Catalyzed C?H Difluoromethylation of Ketoximes: Tuning the Regioselectivity from the meta to the para Position

A highly para-selective CAr?H difluoromethylation of ketoxime ethers under ruthenium catalysis has been developed. A wide variety of ketoxime ethers are compatible with the reaction, which leads to the corresponding para-difluoromethylated products in moderate to good yield. A mechanistic study clearly showed that chelation-assisted cycloruthenation is the key factor in the para selectivity of the difluoromethylation of ketoxime ethers. Density functional theory was used to gain a theoretical understanding of the para selectivity.#.

1, 2, 4-oxadiazole incorporated ketoprofen analogues in search of safer non-steroidal anti-inflammatory agents: Design, syntheses, biological evaluation and molecular docking Studies

Background: Improving the gastrointestinal safety profile of Non-Steroidal Anti- Inflammatory Drugs (NSAIDs) is an important goal. An important strategy to develop NSAIDs with minimal Gastrointestinal (GI) toxicity is to target the COX-2 isoform with a se

Sequential meta-/ortho-C-H Functionalizations by One-Pot Ruthenium(II/III) Catalysis

Sequential twofold meta-C-H/ortho-C-H functionalization was achieved by means of versatile ruthenium(II) biscarboxylate catalysis. The double C-H activation proved viable in a one-pot fashion with the assistance of synthetically useful imidates. The operationally simple twofold C-H functionalization occurred with high levels of positional selectivity control and was conducted in a nonsequential manner by the judicious choice of the reaction temperature. Detailed experimental mechanistic studies, including unprecedented electron paramagnetic resonance (EPR) experiments, provided strong support for homolytic C-X bond cleavage and facile C-H ruthenation, while a computational density functional theory (DFT) analysis was supportive of a novel mechanistic scenario involving synergistic catalysis via cyclometalated ruthenium(III) complexes as key intermediates.

A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation

The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.

Efficient resolution of profen ethyl ester racemates by engineered Yarrowia lipolytica Lip2p lipase

Enzyme-catalyzed enantiomer discrimination is still a great challenge for the development of industrial pharmaceutical processes. For the resolution of ibuprofen, naproxen and ketoprofen racemates, three major anti-inflammatory drugs, only lipases from Candida rugosa present a high selectivity if solvent and surfactant use is discarded. However, their catalytic activities are too low. In the present work, we demonstrate that the lipase Lip2p from the yeast Yarrowia lipolytica has a higher catalytic activity than C. rugosa lipases to hydrolyze the ethyl esters of ibuprofen, naproxen and ketoprofen, but its selectivity is not sufficient [E?=?52 (S); 11 (S) and 1.5 (R) respectively]. The enantioselectivity was further improved by site-directed mutagenesis, targeted at the substrate binding site and guided by molecular modelling studies. By investigating the binding modes of the (R)- and (S)-enantiomers in the active site, two amino acid residues located in the hydrophobic substrate binding site of the lipase, namely residues 232 and 235, were identified as crucial for enantiomer discrimination and enzyme activity. The (S) enantioselectivity of Lip2p towards ethyl ibuprofen esters was rendered infinite (E???300) by replacing V232 by an A or C residue. Substitution of V235 by C, M, S, or T amino acids led to a great increase in the (S)-enantioselectivity (E???300) towards naproxen ethyl ester. Finally, the variant V232F enabled the efficient kinetic resolution of ethyl ketoprofen ester enantiomers [(R)-enantiopreference; E???300]. In addition to the increase in selectivity, a remarkable increase in velocity by 2.6, 2.7 and 2.5?times, respectively, was found for ibuprofen, naproxen and ketoprofen ethyl esters.