- Preparation method of methyl 4-methoxyacetoacetate
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The invention discloses a preparation method of methyl 4-methoxyacetoacetate, belonging to the technical field of organic synthesis. According to the method, sodium methoxide is used as alkali, acetonitrile and methyl tert-butyl ether are used as a mixed solvent, and the reactant methyl 4-chloroacetoacetate is fed in stages, so a reaction temperature is reduced, ester hydrolysis byproducts are prevented from being generated, product quality is improved, production cost is greatly reduced, and economic benefits are improved.
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Paragraph 0025-0038
(2021/04/10)
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- Preparation method of 4-alkoxyacetoacetate compound
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The invention discloses a preparation method of a 4-alkoxyacetoacetate compound, and the method comprises the following steps: reacting a compound I with a first alkali in a first solvent to obtain anintermediate II; reacting the intermediate II obtained in the step (1) with a second alkali in a second solvent to obtain an intermediate III; reacting the intermediate III obtained in the step (2) in an aqueous solution of acid to obtain a product IV, namely the 4-alkoxyacetoacetate compound, wherein X is chlorine, bromine or iodine; wherein R is a C1-C4 alkyl group and a derivative thereof. Thepreparation method provided by the invention has the advantages of simple steps, mild conditions, environmental friendliness, cheap and easily available raw materials, stable supply and low cost, andcreates favorable conditions for reducing the raw material cost of dolutegravir.
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Paragraph 0044; 0047; 0048; 0051; 0052; 0055; 0056; 0059
(2020/04/22)
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- Preparation process of methyl 4-methoxyacetoacetate
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The invention discloses a preparation process of methyl 4-methoxyacetoacetate, comprising the following process steps: step 1, taking anhydrous toluene as a solvent, adding a methanol solution of sodium methoxide in the solvent as a base, at room temperature, dropwise adding methyl 4-chloroacetoacetate in the solvent, after dropwise adding, stirring, heating to 65-70 DEG C during stirring, and reacting for 3 to 5 hours to obtain a sodium salt of methyl 4-methoxyacetoacetate; step 2, acidifying the sodium salt, adjusting with acid to achieve the pH of 5-6, stirring for 30 min, and adjusting thepH to 3-4 to obtain a toluene layer and an aqueous layer, washing the toluene layer to neutral with a saturated sodium chloride solution, performing reduced pressure distillation to remove toluene and obtain a crude product of methyl 4-methoxyacetoacetate, and performing reduced pressure distillation on the crude product to obtain a target product with the purity of 99 percent. The invention discloses the preparation process of methyl 4-methoxyacetoacetate to realize effective, high-quality and low-cost synthesis.
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Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0042
(2019/03/28)
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- NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS
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The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.
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Paragraph 0288; 0289; 0291; 0292
(2019/05/16)
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- Synthetic method of methyl 4-methoxyacetoacetate
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The invention discloses a synthetic method of methyl 4-methoxyacetoacetate. The synthetic method comprises the following specific steps: (1) adding tetrahydrofuran into a reaction kettle, introducing an inert gas, controlling the internal temperature of the reaction kettle to be 15-25 DEG C, adding sodium hydride and potassium methoxide, adding tetrahydrofuran again, controlling the temperature of the system to be 20 DEG C, dropwise adding a mixed solution of methanol and methyl4-chloroacetoacetate for reaction for 4-6 hours, and heating up to 20-25 DEG C for continuous reaction for 3-5 hours; (2) cooling down to -5-0 DEG C, adding hydrochloric acid solution to adjust the pH value of the reaction system to be 10-12, and performing suction filtration on reaction liquid to obtain a white solid; and (3) adding the white solid into ethyl acetate, dropwise adding hydrochloric acid solution at 0 DEG C to adjust the pH of the reaction system to be 3-5, then performing suction filtration on the reaction liquid to separate out an organic layer from the filtrate, decolorizing an organic phase by using a decolorant, and then performing evaporation to remove the solvent, thereby obtaining a pure product namely methyl 4-methoxyacetoacetate. According to the synthetic method disclosed by the invention, reaction can be carried out at room temperature, and a product can be evaporated out at a relatively low temperature, so that the risk of the production process is directly and effectively reduced, and the impurity content of the product is reduced.
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Paragraph 0015; 0016; 0017; 0018; 0019; 0020
(2016/10/17)
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- A 4 - methoxy methyl acetoacetate method for the preparation of
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The invention discloses a 4-methoxy methyl acetoacetate preparation method. The 4-methoxy methyl acetoacetate preparation method comprises the following steps of adding a solvent tetrahydrofuran into a reaction kettle and leading inert gas into the reaction kettle, setting the internal temperature of the reaction kettle to be 15 DEG C to 25 DEG C, adding industrial sodium hydride and a metal alkaline compound in a stirring state, then adding the solvent tetrahydrofuran, dropwise adding mixed liquid of methyl alcohol and methyl-4-chloroacetoacetate at the temperature of lower than 20 DEG C to perform reaction for 4-6 hours, rising the temperature to be 20 DEG C to 25 DEG C to continue to react for 4-15 hours, reducing the system temperature to be 6 DEG C to 10 DEG C after TLC detection reaction is completed, adding a hydrochloric acid solution with molar concentration of 2 mol/L to regulate the pH of a system to be 5 to 7, performing standing and laying, concentrating and spin-drying upper-layer liquid to remove the solvent tetrahydrofuran after liquid separation and then obtaining a colorless product 4-methoxy methyl acetoacetate through wiped-film molecular distillation. The 4-methoxy methyl acetoacetate can react at room temperature, a product can be produced at low temperature through distillation, and dangerousness in the production process and product impurity content can be directly and effectively reduced.
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Paragraph 0034; 0035
(2017/01/02)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF PERIODONTITIS AND RHEUMATOID ARTHRITIS
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The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of periodontitis and rheumatoid arthritis may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection.
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Paragraph 0107; 0108
(2015/05/26)
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- Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation
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A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.
- Allan, Kevin M.,Hong, Boram D.,Stoltz, Brian M.
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supporting information; experimental part
p. 4960 - 4964
(2010/02/15)
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- Method for preparing chiral diphosphines
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The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.
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- Catalytic reduction of ketones and aldehydes using organometallic ruthenium complexes
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Ketones and aldehydes are hydrogenated to the corresponding alcohol or alkyl group, using H2 gas as the stoichiometric reductant, and organometallic ruthenium complexes as the catalysts.
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- Process for preparing optically active oxazolidinone derivative
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Disclosed is a process for preparing an optically active oxazolidinone derivative comprising allowing hydrazine to react on an optically active ester having a hydroxyl group at the 3-position which is represented by formula (II): wherein R1represents a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, a methoxymethyl group, a benzyloxymethyl group, a benzyloxycarbonylaminomethyl group which may have a substituent or substituents on the benzene ring thereof, an acylaminomethyl group having 3 to 10 carbon atoms, or an alkyloxycarbonylaminomethyl group having 3 to 6 carbon atoms; R2and R3, which may be the same or different, each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, an acetylaminomethyl group, a benzoylaminomethyl group, or a benzyl group; and * indicates an asymmetric carbon atom, and subjecting the resulting hydrazide to Curtius rearrangement.
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- Asymmetric hydrogenation method of a ketonic compound and derivative
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The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative. The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative. The process for the asymmetric hydrogenation of a ketonic compound and derivative is characterized in that the asymmetric hydrogenation of said compound is carried out in the presence of an effective amount of a metal complex comprising as ligand an optically active diphosphine corresponding to one of the following formulae: STR1
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- Solid-phase synthesis of pyrrolo[3,4-b]pyridines and related pyridine- fused heterocycles
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Sequential Hantzsch condensation and cyclative cleavage reactions have been used to define a novel solid-phase route to pyrrolo[3,4-b]pyridines and related pyridine-fused heterocycles. A combinatorial library of ~5000 compounds prepared via this chemistry is described.
- Bhandari, Ashok,Li, Bei,Gallop, Mark A.
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p. 1951 - 1960
(2007/10/03)
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- Acetoacetic acid ester derivatives for the manufacture of α-hydroxycarbonyl compounds
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The invention is concerned with a novel process for the manufacture of compounds of the formula STR1 wherein R1 signifies C1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R2 each independently represent hydrogen or C1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl. The process is characterized in that a compound of the formula STR2 wherein R stands for C1-4 -alkoxy, chlorine, bromine or C1-4 -alkanoyloxy, R1 and R2 have the above significance and R3 represents C1-4 -alkyl. is hydrolyzed and subjected to an aldol condensation and, where R=C1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment. The compounds I are for the most part known flavoring substances.
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- Process for the production of 4-alkoxyacetoacetic acid esters
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Process for the production of 4-alkoxyacetoacetic acid esters from 4-chloro or 4-bromoacetoacetic acid esters. 4-chloro or 4-bromoacetoacetic acid ester is reacted with more than one equivalent of an alkali alcoholate in an aprotic solvent effectively at a temperature of 50° to 100° C.
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- REACTIONS OF KETENE ACETALS 16. THE REGIOSPECIFIC SYNTHESIS OF PARTIALLY METHYLATED PURPURINS
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Two novel vinylketene acetals, 1,4-dimethoxy-1,3-bistrimethylsiloxybutadiene and 1,3,4-trimethoxy-1-trimethylsiloxybutadiene have been prepared in view of their eventual application to the synthesis of the antitumor antibiotic bikaverin.Use of the former in the elaboration of anthraquinones has shown that structures proposed for two natural products, purpurin 1-methyl ether and 8-hydroxypurpurin 1-methyl ether are in fact those of anthragallol derivatives.The second diene has afforded confirmation of the nature of xanthorin 5-methyl ether as well as of a degradation product of bostrycin.A substitution pattern claimed for another natural product, 5-hydroxyanthragallol 2,5-dimethyl ether, is also incorrect.
- Simoneau, Bruno,Brassard, Paul
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p. 3767 - 3774
(2007/10/02)
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- Combating arthropods with 3-alkoxymethyl- and-alkylthiomethyl-pyrazol(5)yl(thiono)(thiol)-phosphoric(phosphonic) acid esters and ester-amides
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3-Alkoxymethyl- and -alkylthiomethyl-pyrazol(5)yl(thiono)(thiol)-phosphoric(phosphonic) acid esters and ester-amides of the formula STR1 in which R is hydrogen, alkyl, cyanoalkyl or phenyl, R1 is hydrogen or halogen, R2 is alkoxy or alkylthio, R3 is alkyl, alkoxy, monoalkylamino or phenyl, R4 is alkyl, and X and Y each independently is oxygen or sulphur, which possess arthropodicidal properties.
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- Combating arthropods with N,N-dimethyl-O-[3-(substituted-methyl)-pyrazol-5-yl]-carbamic acid esters
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N,N-Dimethyl-O-[3-(substituted-methyl)-pyrazol-5-yl]-carbamic acid esters of the formula STR1 in which R is hydrogen, alkyl, cyanoalkyl or phenyl, and R1 is alkoxy or alkylthio which possess arthropodicidal properties.
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- 1,4-Dihydropyridine esters
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A new class of 1,4-dihydropyridines which are characterized by the presence of ester substitutes at positions 3 and 5 of the nucleus and by the presence of an alkoxyalkyl at position 2. The products exhibit coronary activity and have particular application as coronary dilators, antifibrillators, anti-hypertensives, and as muscular and vascular spasmolytics.
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