81576-57-0

Basic information

• Product Name: (R)-ibuprofen methyl ester
• Synonyms: (R)-ibuprofen methyl ester
• CAS NO: 81576-57-0
• Molecular Weight: 220.312
• Mol File: 81576-57-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-ibuprofen methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ibuprofen methyl ester(81576-57-0)
• EPA Substance Registry System: (R)-ibuprofen methyl ester(81576-57-0)

Safety Data

• Hazardous Substances Data: 81576-57-0(Hazardous Substances Data)

Upstream product

• 51146-57-7 (R)-ibuprofene 
• 67-56-1 methanol 
• 113544-36-8 (R)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 186581-53-3 diazomethane 
• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 67511-12-0 methyl 2-(4-isobutylphenyl)acrylate 
• 59771-01-6 1-(para-isobutyl phenyl)-1-bromoethane 
• 40150-92-3 1-(4-isobutylphenyl)ethanol 
• 41283-72-1 ibuprofen ethyl ester 
• 5445-17-0 Methyl 2-bromopropionate 
• 2051-99-2 1-bromo-4-isobutylbenzene 
• 15687-27-1 ibuprofen 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 51146-56-6 (S)-ibuprofen 
• 51146-57-7 (R)-ibuprofene 
• 709040-13-1 (R) (-)-dimethyl-3-(4-isobutylphenyl)-2-oxobutan-1-phosphonate 
• 114937-04-1 (4R)-2-<(1R)-1-(4-(2-Methylpropyl)phenyl)ethyl>thiazolidine-4-carboxylic Acid 
• 114937-27-8 (2R)-2-<4-(2-Methylpropyl)phenyl>propanal 
• 93673-13-3 (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol 

Relevant articles and documents

Synthetic method of chiral 2-aryl propionate

The invention belongs to the technical field of chemical synthesis, and relates to a synthetic method of chiral 2-aryl propionate, in particular to enantioselective synthesis of 2-aryl propionate. Thesynthetic method comprises the following steps: adding a copper salt, a chiral phosphine ligand, a silicon-hydrogen compound (in terms of SiH), ROH and 2-aryl acrylate in a certain ratio into a reaction bottle, carrying out a reaction in a reaction solvent at -50 to 40 DEG C for 0.25-6 h, and successively performing hydrolyzing, liquid separating, extracting, washing, drying and column chromatography after the reaction is finished, thereby obtaining the target compound 2-aryl propionate. Compared with the prior art, the method has the advantages that the 2-aryl acrylate is reduced by adopting a Cu catalytic system, a catalyst, namely a Cu compound is low in price, and the limitation of hydrogen high-pressure reduction and a noble metal catalyst is broken through. Chiral 2-aryl propionic acid can be obtained through a simple hydrolysis reaction of 2-aryl propionate, and a part of the compounds of 2-aryl propionate are effective components of current commercially-available drugs suchas ibuprofen and naproxen.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n＝0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)

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.

Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes

Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic α-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral α-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic α-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S)-ibuprofen (99:1 er) via hydrolysis and recrystallization.

Optimized hybrid nanospheres immobilizing Rhizomucor miehei lipase for chiral biotransformation

In this study, the immobilization of Rhizomucor miehei lipase into hybrid nanospheres containing a liposomal core was reported. Organic internal liposomal enzyme phase was protected by inorganic silica matrix, obtained with and without surfactant, that st

Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose

Here we report the stereoselective hydrolysis of racemic esters catalyzed by Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) immobilized on octyl-sepharose via physical adsorption. Hydrophobic immobilization caused to almost six fold hyperactivation with 229.2 and 81.3 U/mg enzyme for immobilized CRL and ROL, respectively (13.2 and 48.75 U/mg for corresponding free enzyme). Based on the preliminary results, CRL was chosen for further investigation. The performance and yield of the reaction were evaluated as a function of the critical reaction parameters such as temperature, enzyme to substrate ratio and organic co-solvent. An increase in the temperature resulted to decrease in enantioselectivity of hydrolysis reaction. The hydrolysis reactions were carried out in presence of two organic solvents; n-hexane and isooctane. Generally n-hexane was a better co-solvent compared to isooctane. High enantioselective hydrolysis of the racemic esters (yielding S(+) ibuprofen; ee ≤ 95%) can be achieved using the immobilized CRL. Among various esters the kinetic resolution of ibuprofen butyl ester yielded the best results (E value 70 and 74; conversion 14.6 and 8.9 in n-hexane and isooctane, respectively). The immobilized derivatives were re-used in four cycles and showed little decrease in enantiomeric excess of (S)-ibuprofen. 96.7 eep and conversion 14.6 in first cycle reached to 90.5 eep and conversion 11.3 in the forth cycle.

Catalytic methyl transfer from dimethylcarbonate to carboxylic acids

Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and green potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols, and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.

Enantioselective hydrogenation of α-substituted acrylic acids catalyzed by iridium complexes with chiral spiro aminophosphine ligands

Highly active: Iridium complexes with chiral spiro aminophosphine ligands were synthesized and applied as catalysts for the asymmetric hydrogenation of α-substituted acrylic acids (see scheme). The complexes were highly active catalysts, showing turnover frequencies of up to 6000 h-1, and catalyst loadings could be reduced to 0.01 mol %. Copyright

Ene reductase-catalysed synthesis of (R)-profen derivatives

Enantiomerically pure (R)-profen derivatives and intermediates are synthesised utilising the enzyme YqjM, an ene reductase from Bacillus subtilis. After optimisation of the reaction conditions, the chemoenzymatic approach was applied for the first time in the synthesis of (R)-flurbiprofen methyl ester. Copyright

Improvements of enzyme activity and enantioselectivity in lipase-catalyzed alcoholysis of (R,S)-azolides

With Candida antarctica lipase B (CALB)-catalyzed alcoholysis of (R,S)-naproxenyl 1,2,4-triazolide at the optimal conditions (i.e. anhydrous MTBE as the solvent, and methanol as the acyl acceptor at 45°C) as the model system, the enzyme enantioselectivity