45 results about "Swern oxidation" patented technology

The invention discloses a synthesizing method of 1-benzyl-piperidone hydrochloride. The method comprises steps that: (1) 3-hydroxypyridine is added to an organic solvent, and is refluxed under a temperature of 100 to 110 DEG C; benzyl halide is dropped into the solution, and the refluxing reaction is continued for 2 to 4 hours, such that a product A is obtained; (2) the product A is added to an alcohol organic solvent; sodium borohydride is added to the solution under an ice bath; the temperature of the solution is recovered to room temperature; the solution is stirred for 10 to 15 hours; the reaction liquid is quenched by using water; the alcohol organic solvent is removed; the pH value of the solution is regulated to 1-2 by using strong acid; the solution is extracted by using an extractant, and a water phase is preserved; the pH value of the solution is regulated to 13-14 by using an alkali solution, such that a product B is obtained; (3) through a Swerns oxidation reaction, hydroxyl groups in the product B are oxidized into ketone groups; the product is washed; an organic phase is dried, filtered, and condensed; an ethyl acetate hydrochloride solution is added to the product until the pH value is 1-2; the product is stirred and cooled; when solid is completely precipitated, the product is filtered and dried by baking, such that 1-benzyl-piperidone hydrochloride is obtained. The invention is advantaged in low cost and safe operation.

The invention relates to a new synthesis route and method of a bedaquiline racemate, and belongs to the medical technical field. The method comprises the steps: (1) carrying out a reaction of a starting material 3-bromobenzyl-6-bromo-2-methoxyquinoline (II) with metal magnesium in THF to prepare a Grignard reagent, then adding 1-naphthaldehyde (III) in the prepared Grignard reagent, carrying out a reflux reaction to obtain a compound (IV) 2-(6-bromo-2-methoxyquinoline-3-yl)-1-(naphthalen-1-yl)-2-phenylethanol; (2) undergoing swern oxidation of the compound (IV) to obtain a carbonyl compound 2-(6-bromo-2-methoxyquinoline-3-yl)-1-(naphthalen-1-yl)-2-phenyl ethyl ketone (a compound V); and (3) carrying out a Grignard reaction of the compound (V) with the Grignard reagent (VI) to obtain the bedaquiline racemate (I). The method is simple in route, is mild in reaction conditions, low in cost, high in yield, and suitable for industrialized production application.

The invention relates to a preparation method of paricalcitol, which is characterized in that after hydroxyl in the vitamin D2 is protected by p-toluenesulfonates, in the presence of alkali, intramolecular cyclization reaction happens in methanol to generate a compound 5; the compound 5 undergoes allylic oxidation and hydroxyl is protected to obtain a key intermediate 7; in the presence of ozone,the side chains and exocyclic terminal double bonds of the key intermediate 7 are cut off to obtain a compound 8; the primary hydroxyl in the compound 8 is selectively protected, a three-membered ring is opened in the presence of acid and then hydroxyl is protected to obtain a key intermediate 11; after the secondary hydroxyl in the key intermediate 11 is protected by sulphonate, a compound 12 isobtained through reduction by LiAlH4; a compound 13 is obtained after the compound 12 is subjected to Swern oxidation and carries out Wittig reaction with the compound 12 to obtain a compound 14; andthe target compound can be obtained by removing the protective group in the compound 14. The reagents used in the method are simple and are convenient to operate, the reactions concerning regioselectivity and stereoselectivity are few, the route is shorter and 12 steps of reactions are carried out.

The invention discloses 4-(2-(2-methyl sulfoxide)ethyl)-4-nitrobenzene)morpholine shown in the formula (I) and preparation and application thereof. A preparation method includes the steps that 2-(2-chlorine-5 nitro)phenethyl alcohol shown in the formula (II) and morpholine are mixed to prepare 2-(2-morpholine-5-nitrobenzene)ethanol shown in the formula (III); bis(trichloromethyl)carbonate ester, a sodium methyl mercaptide aqueous solution and an aqueous hydrogen peroxide solution are sequentially added dropwise to 2-(2-morpholine-5-nitrobenzene)ethanol shown in the formula (III), and finally 4-(2-methyl sulfoxide)ethyl)-4-nitrobenzene)morpholine is prepared. According to the application of 4-(2-methyl sulfoxide)ethyl)-4-nitrobenzene)morpholine, the obtained Swern reagent reacts with an alcohol compound shown in the formula (IV), and aldehyde or ketone is prepared after after-treatment. The defects of an existing Swern oxidation method are overcome, generation of a stink byproduct dimethyl sulfide and toxic carbon monoxide is avoided from the source, the reaction temperature is increased to be -30 DEG C to 0 DEG C, and an odorless byproduct novel sulfur ether can be recycled and reused. The formulas are shown in the description.

The invention provides a method for synthesizing a natural product Tarchonanthuslactone isomer. According to the method, methyl-3-hydroxybutyrate is used as a raw material, and PMB ester protection, LiALH4 reduction, Swern oxidation, Mukaiyama Aldol reaction, ester hydrolysis, Yanaguchi cyclization, de-protection and condensation are performed, so that the natural product Tarchonanthuslactone isomer is obtained. The synthetic route is novel and reasonable in design, the raw materials are cheap and easy to obtain, the operation process is simple and convenient, the reaction condition is mild, the rate is high, side reaction is less, the operation is simple and convenient, and the synthesizing cost is greatly reduced.

The invention relates to a preparation method of tert-butyl-5-(hydroxymethyl)-7-oxa-2-azaspiro[3.5]nonane-2-formate, and mainly solves the technical problem that no proper industrial synthesis methodexists at present. The product is synthesized by six steps, and the preparation method comprises the steps: a first step, a compound 1 is subjected to Swern oxidation reaction to generate a compound 2; a second step, a compound 3 is obtained through a Horner-Wadsworth-Emmons reaction; a third step, a compound 4 is obtained through Michael addition; a fourth step, a compound 5 is obtained through reduction of the compound 4 with lithium tetrahydroaluminum; a fifth step, the compound 5 is dehydrated and retained with a ring to obtain a compound 6 under the action of sodium hydrogen; and a sixthstep, hydrogenation is preformed to remove a protective group, and then a protective group is added to obtain the target compound 7. The obtained compound is a useful intermediate or product for synthesis of many drugs.

The invention belongs to the field of chemical synthesis. The invention relates to a method of synthesis of 6-deoxy-L-talose,including: 1) performing glucoside protection of 1-positon hydroxyl of L-rhamnose in methanol solution by utilizing cation exchange resin (732H+type) to obtain a compound; 2) performing isopropylidene protection of hydroxyls at 2 and 3 positions of the compound to obtain a compound; 3) oxidizing 4-position hydroxyl of the compound to a ketone carbonyl group by utilizing a Swern oxidation system, so as to obtain a compound; 4) performing stereoselective reduction of 4-position carbonyl of the compound by utilizing sodium borohydride or sodium cyanoborohydride, so as to obtain a precursor compound with an opposite configuration to the raw materials, of 6-deoxy-L-talose; 5) refluxing the compound in sulfuric acid aqueous solution to hydrolyze to obtain 6-deoxy-L-talose. The preparing method using easily-available L-rhamnose having low price as the initial raw material, is a simple method, and is utility and efficient.

The invention belongs to the technical field of drug synthesis, and relates to a preparation method of a novel anticancer drug lanosterol derivative. According to the method, an intermediate LD-a is generated by taking lanosterol as a starting raw material under the protection of tert-butyl dimethyl silicon (TBS); a Sharpless asymmetric dihydroxylation reaction is carried out on the intermediate LD-a under the action of osmium tetroxide (OsO4), and a vicinal diol compound LD-b is generated; Swern oxidation is carried out on the LD-b compound under the a triethylamine alkaline condition, and aalpha-hydroxy-ketone compound LD-c is generated; an acylation reaction is carried out on the LD-c with acetic anhydride, and an intermediate LD-d is obtained; the intermediate LD-d is subjected to TBSremoval protection, and an intermediate LD-e is obtained; and finally, the target lanosterol derivative LD is obtained through epoxidation. According to the invention, the reaction conditions of allthe steps are relatively mild, the synthetic steps are short, the use of highly toxic or expensive reagents is avoided, the prepared product is high in purity, and the preparation method can be applied to industrial production.

The invention relates to a preparation method for trace tritiated biotoxin deoxynivalenol. The method comprises the following steps: using the deoxynivalenol as a raw materials, and phenylboronic acid to protect 7 alpha-position and 15-position hydroxies, and oxidizing 3-position hydroxyl through Swern Oxidation; using isopropyl alcohol as a resolvent, and adopting tritiated sodium boro-hydride to selectively reduce the 3-position carboxide, so as to obtain tritiated deoxynivalenol. The method has the advantages that the raw materials are easy to obtain, the reaction condition is mild, the operation is easy, and the obtained tritiated compound is clear in labeling position and stable; the chemical purity and the radiochemical purity of the product are not less than 98 percent, and the specific activity is 2.52 Ci/mmol. The method provides an important material foundation for carrying out poison mechanism and food safety evaluation of the deoxynivalenol in a deep-going way.

The invention relates to a method for preparing a clausenamide intermediate by a Swern oxidation process and belongs to the field of pharmaceutical chemicals. The method comprises a step of oxidizing N-methyl-N-(2-hydroxy-2-phenyl)ethyl-3-phenylglycidylamide (I) compound under an alkaline condition in a solvent to obtain a N-methyl-N-benzoylmethyl-3-phenylglycidylamide(II) compound.

The invention relates to a tulathromycin synthesis method. The method comprises the steps of (1) carrying out a reaction on norazithromycin and Fmoc-Cl under the action of an acid-binding agent to selectively prepare a 2'-Fmoc-norazithromycin intermediate; (2) oxidizing a C-cyclic alcohol hydroxyl group of the 2'-Fmoc-norazithromycin intermediate by utilizing a Swern oxidation reaction, so as to prepare a 4''-oxo-2'-Fmoc-norazithromycin intermediate; (3) under the action of strong base, enabling trimethylsulfur iodide to react with the 4''-oxo-2'-Fmoc-norazithromycin intermediate, so as to prepare a 4''-methyleneepoxy-2'-Fmoc-norazithromycin intermediate; and (4) under the condition of an organic solvent, enabling the 4''-methyleneepoxy-2'-Fmoc-norazithromycin intermediate to react with n-propylamine, so as to obtain target product tulathromycin. Compared with the prior art, the method has the advantages that the reaction selectivity is high, the monitoring is convenient, the reaction steps are shortened, the problems of production safety and heavy metal residue possibly existing in catalytic hydrogenation by using noble metal are avoided, and the production cost is reduced while the reaction efficiency is improved.

Described is a process of preparing 3-aryl, 4-aryloxy furan-5- ones which are useful as inhibitors of cyclooxygenase-2(COX-2). Such compounds are useful as anti-inflammatory agents. The process is directed to an asymmetric synthesis which involves: a trisubstituted styrene derivative preparation via Horner-Wadsworth-Emmons reaction and subsequent one pot trifluoromethylation of the allylic alcohol; preparation of the alpha -hydroxyl ketone using Sharpless assymmetric dihydroxylation and Swern oxidation; the esterification of the alpha -hydroxyl ketone with the phenoxy acetic acid; and the Dieckman condensation of the resulting ester.

The invention belongs to the field of medicine synthesis, and relates to a preparing method of a miglitol intermediate. The method includes performing Swern oxidation by adopting tetrabenzyl glucose diol as a raw material to obtain a tetrabenzyl glucose dicarbonyl derivative, and directly subjecting the oxidation product without separation to a double reductive amination reaction with ethanolamine and sodium cyanoborohydride under the existence of a dehydrant to prepare tetrabenzyl miglitol that is an important intermediate for preparation of miglitol. The method is mainly advantageous in that: the tetrabenzyl glucose dicarbonyl derivative which is instable is directly used for the reaction in the next step without separation; proper reaction conditions are selected in the double reductive amination reaction step to directly obtain an optically pure target product 2-position of which is in an R configuration; steps of separation and purification for an enantiomer mixture are omitted, and loss caused by the steps is omitted; and the method is short in reaction time and high in yield.

The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.