cas 95530-58-8, (R)-(+)-4-Isopropyl-2-oxazolidinone

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Simple preparation method of N-acyl compound
The invention relates to a simple preparation method of an N-acyl compound. The simple preparation method comprises the specific steps that an amine compound and R-OCF3 are mixed in a solvent and react for 1 min-48 h at -80-100 DEG C, after the reaction is completed, water is added for quenching, and column separation and purification or recrystallization and purification are carried out to obtainthe N-acyl compound. According to the simple preparation method of the N-acyl compound, the characteristic that a substance containing trifluorooxygen groups can be decomposed in situ to produce fluorophosgene is utilized, and the substance directly reacts with the amine compound to achieve rapid N-carbonylation of an amines substrate and efficiently prepare a urea derivative and a carbamyl fluoride compound. The simple preparation method of the N-acyl compound has the advantages that the operation is simple, the reaction time is short, the application range of the substrate is wide, no catalysts or additives need to be used, the raw materials are easy to obtain, the product yield is high, the purification is easy, and the required compound can be obtained by using a column chromatographyisolation method or recrystallization.
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Paragraph 0049-0051

(2019/07/04)

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information
p. 10907 - 10912
(2019/08/02)

Synthetic method and application of chiral compound
The invention relates to a synthetic method of a chiral compound. The synthetic method comprises the following steps: taking 0.2720g of zinc chloride as a catalyst under water-free and oxygen-free conditions, weighing 2.0449g of acetylurea and 8.1397g of
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Paragraph 0008; 0009

(2017/10/25)

Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: Synthesis of (+)-1,4-dideoxyallonojirimycin
Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine iminosugar (+)-1,4-dideoxyallonojirimycin.
Ferreira, Jasmin,Rees-Jones, Sophie C. M.,Ramaotsoa, Valerie,Msutu, Ath'enkosi,Hunter, Roger
p. 1545 - 1549
(2016/02/09)

Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates
Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.
Casiello, Michele,Iannone, Francesco,Cotugno, Pietro,Monopoli, Antonio,Cioffi, Nicola,Ciminale, Francesco,Trzeciak, Anna M.,Nacci, Angelo
p. 8 - 14
(2015/07/01)

Synthesis of salicylic acid-based 1,3,4-oxadiazole derivatives coupled with chiral oxazolidinones: Novel hybrid heterocycles as antitumor agents
A series of novel salicylic acid-based 1,3,4-oxadiazoles derivatives coupled with chiral oxazolidinones were synthesized to screen for their in vitro antitumor activity against five human cancer cell lines. Some of these compounds showed good antitumor activities with IC50values ranging from 31.19-57.21 μM. Among the tested compounds 11, 15, 19,23,24, and 34 showed broad-spectrum antitumor activity against all the cell lines. In particular, compound 19 revealed remarkable antitumor activity with IC50 = 31.19-41.87 μM. A431 was the most sensitive cell line against all the compounds studied, followed by HeLa, MCF-7, A549 and HepG2. Structures of newly synthesized compounds were confirmed by IR,1 H NMR, 13C NMR and HRMS spectral data
Murty,Penthala, Raju,Nath, Lekshmi R.,Anto, Ruby John
p. 1133 - 1142
(2015/03/31)

An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular schmidt/bischler-napieralski/imine-reduction cascade sequence
A novel enantioselective strategy for the total synthesis of (S)-tylophorine was developed in an overall yield of 48% with more than 99% ee from readily avaliable azido acid and phenanthryl alcohol. This route features an Evans stereoselective alkylation and an unprecedented one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence, in which three new bonds and two rings formed in 84% yield. The intramolecular Schmidt rearrangement of the azido aldehyde was proved to be racemization-free.
Su, Bo,Chen, Fazhong,Wang, Qingmin
p. 2775 - 2779
(2013/04/24)

Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2
Dehydrative synthesis of oxazolidinones from amino alcohols and CO 2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO 2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process.
Foo, Siong Wan,Takada, Yuki,Yamazaki, Yusuke,Saito, Susumu
supporting information
p. 4717 - 4720
(2013/08/23)

Synthesis of some 2-Oxazolidinones in mild conditions
One step efficient protocol for the synthesis of 2-oxazolidinones in paste chemical medium is described under microwave activation with 80 % yield.
Bratulescu, George
experimental part
p. 929 - 930
(2011/12/15)

On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one
The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[α]D26 = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[α]D26 = - 16.1 (c 5.2, EtOH)}.
Benoit, David,Coulbeck, Elliot,Eames, Jason,Motevalli, Majid
p. 1068 - 1077
(2008/09/20)

Efficient synthesis of oxazolidin-2-one via (chitosan-Schiff base)cobalt(II)-catalyzed oxidative carbonylation of 2-aminoalkan-1-ols
The (chitosan-Schiff base)cobalt(II) complex was found to be an efficient catalyst for the oxidative carbonylation (CO/O2) of 2-aminoalkan-1-ols 1 to give oxazolidin-2-ones 2, in the presence of NaI. The effects of promoters, temperature, solvents, and other reaction conditions were investigated in this study.
Liu, Jianming,Sun, Wei,Zheng, Shuzhan,Xia, Chungu
p. 1593 - 1598
(2008/02/09)

Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols
2-Oxazolidinones are synthesized in high yield by oxidative carbonylation of β-amino alcohols using salen-Co(II)/NaI or salen-Co(III)-I as a catalyst and using CO as the carbonyl source. Studies of functional group compatibility using a series of substituted salen-Co(II) or salen-Co(III)-I complexes demonstrate a broad tolerance of functionality during the carbonylation reaction.
Liu, Jian-Ming,Peng, Xin-Gao,Liu, Jian-Hua,Zheng, Shu-Zhan,Sun, Wei,Xia, Chun-Gu
p. 929 - 932
(2008/02/04)

An efficient synthesis of organic carbonates using nanocrystalline magnesium oxide
An efficient and selective synthesis of organic carbonates using nanocrystalline magnesium oxide has been realized by the direct condensation of alcohols and diethyl carbonate. The catalyst is quantitatively recovered by simple centrifugation and can be reused for four cycles with almost consistent activity.
Kantam, M. Lakshmi,Pal, Ujjwal,Sreedhar,Choudary
p. 1671 - 1675
(2008/02/11)

Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters
Racemic Evans' oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, leading to products with predictable configurations.
Boyd, Ewan,Coulbeck, Elliot,Coumbarides, Gregory S.,Chavda, Sameer,Dingjan, Marco,Eames, Jason,Flinn, Anthony,Motevalli, Majid,Northen, Julian,Yohannes, Yonas
p. 2515 - 2530
(2008/03/15)

Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation
Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright
Birman, Vladimir B.,Jiang, Hui,Li, Ximin,Guo, Lei,Uffman, Eric W.
p. 6536 - 6537
(2007/10/03)

Chemically modified mutant serine hydrolases show improved catalytic activity and chiral selectivity
This invention provides novel chemically modified mutant serine hydrolases that catalyze a transamidation and/or a transpeptidation and/or a transesterification reaction. The modified serine hydrolases have one or more amino acid residues in a subsite replaced with a cysteine, wherein the cysteine is modified by replacing the thiol hydrogen in the cysteine with a substituent group providing a thiol side chain comprising a moiety selected from the group consisting of a polar aromatic substituent, an alkyl amino group with a positive charge, and a glycoside. In particularly preferred embodiments, the substitutents include an oxazolidinone, a C1 to C15 alkyl amino group with a positive charge, or a glycoside.
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(2008/06/13)

Synthesis of 2-oxazolidinone catalyzed by palladium on charcoal: A novel and highly effective heterogeneous catalytic system for oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol
Oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol to synthesize corresponding 2-oxazolidinones catalyzed by a Pd/C-I2 heterogeneous catalytic system has been developed which gave excellent selectivity and high turnover frequency (TOF) values 15 times larger than the best results previously reported. The catalyst could be reused for five times almost without losing its catalytic activity and selectivity. The effects of promoters, pretreatment, solvents, and reaction conditions have been investigated.
Li, Fuwei,Xia, Chungu
p. 542 - 546
(2007/10/03)

Chemical fixation of carbon dioxide co-catalyzed by a combination of Schiff bases or phenols and organic bases
Binaphthyldiamino, ethyldiamino and cyclohexyldiamino Schiff bases can catalyze the reaction of epoxides with carbon dioxide in the presence of catalytic amounts of various organic bases to give the corresponding cyclic carbonates in high yields. The simplest binaphthyldiamino Schiff base, derived from the reaction of binaphthyldiamine with salicylaldehyde, gave the highest yield of cyclic carbonate. This catalytic system can be further simplified by use of a phenol instead of the Schiff base to give the corresponding cyclic carbonates in high yields as well. Mechanistic insights were obtained based on a deuterium labeling experiment, The reaction of aziridines with CO2 and epoxide with CS2 were also examined under the same reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Shen, Yu-Mei,Duan, Wei-Liang,Shi, Min
p. 3080 - 3089
(2007/10/03)

Mechanistic study on nitrosation-deaminocyclization of mono-carbamoylated vicinal amino alcohols and diols: a new preparative in situ formation of ethanediazo hydroxide for the ethylation of carboxylates under mild conditions
While the cyclization of N-carbamoylamino alcohols into oxazolidinones via the activation with NO(1+) underwent smoothly, we found that similar reactions of vicinal diol monocarbamates were very slow. Mechanistic studies by means of time-resolved IR measurements of the former reaction suggested that the initial O-nitrosation was the rate-determining step. Indeed, the introduction of an ethyl group on the nitrogen terminus of diol monocarbamate promoted the desired cyclic carbonate formation. The concomitantly formed ethanediazo hydroxide, the precursor of the protonated form of diazoethane, was evidenced by trapping with p-nitrobenzoic acid as an ethyl ester. The formation of ethyl ester accelerates the reaction in an irreversible manner. Based on an elaboration of the substrates and reaction conditions, 2,3-dimethyl-2,3-butanediol mono-N-ethyl-N-nitrosocarbamate, which is easily prepared in situ from the corresponding ethylcarbamate and t-butyl nitrite, was developed as a new ethylation reagent of various carboxylic acids under mild conditions.
Suzuki, Masumi,Sugai, Takeshi
p. 1217 - 1228
(2007/10/03)

MONOCYCLIC ANILIDE SPIROHYDANTOIN CGRP RECEPTOR ANTAGONISTS
The present invention is directed to compounds that are antagonists of CGRP receptors and that are useful in the treatment or prevention of diseases in which the CGRP is involved, such as headache, migraine and cluster headache. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.
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Page 34-35

(2010/02/08)

Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone.
[reaction: see text] Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and toloxatone.
Mallesham,Rajesh,Reddy, P Rajamohan,Srinivas,Trehan, Sanjay
p. 963 - 965
(2007/10/03)

An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones
A highly efficient oxidative cyclocarbonylation of β-amino alcohols and 2-aminophenol to oxazolidin-2-ones has been achieved by using PdI2 in conjunction with KI as the catalytic system in DME under relatively mild conditions (100 °C and 20 atm of a 4:1 mixture of CO and air).
Gabriele, Bartolo,Mancuso, Raffaella,Salerno, Giuseppe,Costa, Mirco
p. 601 - 604
(2007/10/03)

Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction
Here we report a new catalytic asymmetric synthesis of oxazolidin-2-ones 4 and Cbz-protected 1,2-amino alcohols 5. Our sequence is based on the chemistry of previously unknown 5-acyloxy-oxazolidin-2-ones, which are obtained via proline-catalyzed direct asymmetric three-component Mannich reaction and Baeyer-Villiger oxidation.
Pojarliev, Peter,Biller, William T.,Martin, Harry J.,List, Benjamin
p. 1903 - 1905
(2007/10/03)

Direct organo-catalytic asymmetric α-amination of aldehydes - A simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids
L-Proline as the catalyst: The first direct asymmetric α-amination of aldehydes using L-proline as the catalyst is presented (see scheme; Pg = protecting group). This new reaction gives easy access to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids from simple and easily available starting materials and catalysts. The reactions proceed in high yields and excellent enantioselectivities with as little as 2 mol % of the catalyst.
Bogevig, Anders,Juhl, Karsten,Kumaragurubaran, Nagaswamy,Zhuang, Wei,Jorgensen, Karl Anker
p. 1790 - 1793
(2007/10/03)

Palladium-catalyzed electrochemical carbonylation of 2-amino-1-alkanols to oxazolidin-2-ones under very mild conditions
A new procedure for an efficient synthesis of oxazolidin-2-ones was developed. 2-Amino-1-alkanols undergo oxidative carbonylation under atmospheric pressure of carbon monoxide at room temperature using Pd(II) catalyst in combination with its anodic recycling at a graphite electrode.
Chiarotto, Isabella,Feroci, Marta
p. 3451 - 3453
(2007/10/03)

The reaction of 1,2-amino alcohols with carbon dioxide in the presence of 2-pyrrolidone electrogenerated base. New synthesis of chiral oxazolidin-2-ones
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Casadei, M. Antonietta,Feroci, Marta,Inesi, Achille,Rossi, Leucio,Sotgiu, Giovanni
p. 4759 - 4761
(2007/10/03)

N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction
Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.
Suzuki, Masumi,Yamazaki, Takahiro,Ohta, Hiromichi,Shima, Kyoko,Ohi, Katsuhide,Nishiyama, Shigeru,Sugai, Takeshi
p. 189 - 192
(2007/10/03)

Chiral electrophilic 'glycinal' equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones
The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as α-aminoaldehyde templates useful for the synthesis of a wide variety of optically active α-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones.
Matsunaga, Hirofumi,Ishizuka, Tadao,Kunieda, Takehisa
p. 1275 - 1294
(2007/10/03)

Structure-activity relationships of unsaturated analogues of valproic acid
The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED50 or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.
Palaty,Abbott
p. 3398 - 3406
(2007/10/02)

Practical Preparation of Chiral 4-Substituted 2-Oxazolidinones
A versatile and practical route to both enantiomers of a wide variety of 4-substituted 2-oxazolidinones from the parent heterocycle is provided by regioselective substitutions via 4-methoxy derivative followed by chromatographic separation of the diastereomers derived from N-2-exo-methoxy-1-apocamphanecarbonylation.
Ishizuka, Tadao,Kimura, Koreichi,Ishibuchi, Seigo,Kunieda, Takehisa
p. 991 - 994
(2007/10/02)

Versatile routes to chiral 4-substituted 2-oxazolindinones and α-amino acids. Use of chiron, [4 + 2] cycloadducts of dialkyl azodi-carboxylates and 2-oxazolones
The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones with dialkyl azodicarboxylates results in exclusive formation of [4 + 2] type cycloadducts with moderate levels of diastereofacial selection, which serve as versatile chiral synthons for a wide variety of 4-alkyl and 4-alkyl-2-oxazolidinones as well as α-amino acids.
Matsunaga,Ishizuka,Marubayashi,Kunieda
p. 1077 - 1079
(2007/10/02)

Renin inhibitors having all retro-inverted peptide bonds
Renin-inhibiting peptides of the formula STR1 in which X represents a group of the formula STR2 represents hydroxyl, alkoxy having up to 8 carbon atoms, benzyloxy or a group of the formula --NR4 R5, A, B, D and E are identical or different and in each case represent a direct bond, represent a radical of the formula STR3 in which Q1 denotes oxygen, sulphur or the methylene group represent a grouping of the formula STR4 m represents a number 0, 1 or 2, and L represents a group of the formula --CH2 NR2 R3 and physiologically acceptable salts thereof.
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(2008/06/13)

A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM
Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.
Yoshida, Tohru,Kambe, Nobuaki,Ogawa, Akiya,Sonoda, Noboru
p. 137 - 148
(2007/10/02)

Synthesis of Optically Active cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic Acid via Intramolecular Alkylation of a Chiral Enolate
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Kleschick, William A.,Reed, Michael W.,Bordner, Jon
p. 3168 - 3169
(2007/10/02)

Intramolecular 'Ene' Reactions of Transient, Allylic, and Homoallylic C-Nitrosoformate Esters
Various allylic and homoallylic alcohols have been treated succesively with phosgene and hydroxylamine to form the corresponding N-hydroxycar bamic esters (3).Oxidation of these hydroxamic acid derivatives with sodium or tetraethylammonium periodate in the presence of cyclopentadiene gave the cycloadducts (5) derived from transient allylic and C-nitrosoformate esters (4) and cyclopentadiene.When the cycloadducts were heated in benzene at 80 degree C, or toluene at 111 degree C, they dissociated and the C-nitrosoformate esters underwent intramolecular 'ene' reactions to give hydroxamic acid derivatives having newly formed, five- six- or seven-membered heterocyclic rings.
Kirby, Gordon W.,McGuigan, Henry,McLean, David
p. 1961 - 1966
(2007/10/02)