122 results about "Sulfinamide" patented technology

The invention provides a chiral sulfinylamine monophosphine and a preparation method thereof. The preparation method comprises the following steps: carrying out a condensation reaction of 2-disubstituted phosphinoaryl(heteroaryl)formaldehyde (ketone) 2 and chiral sulfonamide 3 to obtain a compound 4, and reacting the compound 4 with a nucleophilic reagent to prepare a compound 1; or carrying out a condensation reaction of aldehyde (ketone) 5 and the chiral sulfonamide 3 to obtain imine 6, and reacting the imine 6 with a 2-disubstituted phosphinoaryl(heteroaryl) metal reagent to obtain the compound 1; or reacting the imine 6 with the 2-disubstituted phosphinoaryl(heteroaryl) metal reagent to obtain a compound, and reducing the compound to obtain the compound 1; or carrying out a condensation reaction of 2-substituted phosphinoaryl(heteroaryl)formaldehyde (ketone) 8 and the chiral sulfonamide 3 to obtain an imine compound 9, reacting the imine compound 9 with the nucleophilic reagent to obtain a compound 7, and reducing the compound 7 to obtain the compound 1. Different chiral sulfenamides and different metal reagents are used to conveniently obtain the optically pure compound of four configurations comprising (R,R), (R,S), (S,S) and (S,R). The above ligand has the advantages of simple skeleton, synthesis convenience and easy reconstruction, can be applied in various metal-catalyzed asymmetric reactions, and has a very high reaction activity and stereoselectivity.

The invention discloses a high-throughput polyamide nanofiltration composite membrane and a preparation method thereof, which belong to the field of polymeric membrane materials. The composite membrane is prepared by the interfacial polymerization reaction between 5-(N-sulfonamido)isophthaloyl dichloride or a mixture of 5-(N-sulfonamido)isophthaloyl dichloride and 1,3,5-trimesoyl chloride and piperazine monomer, and can be widely used in a water softening process for removing bivalent cations such as Ca<2+> and Mg<2+>. The high-throughput polyamide nanofiltration composite membrane is structurally provided with an ultrathin (10nm) release layer, surface charge are low in electronegativity, the membrane surface property is smooth and hydrophilic, high throughput is shown in terms of properties, the high-throughput polyamide nanofiltration composite membrane has an excellent trapping effect on bivalent and polyvalent cations and good pollution resistance, and the high-throughput polyamide nanofiltration composite membrane can be widely applied in high-throughput domestic water purifiers, sea water desalination, brackish water pretreatment, removal of COD (chemical oxygen demand) suchas dye molecules and phenol molecules in wastewater, separation of dye/salt and material separation and concentration processes in pharmaceutical and food industries.

The invention discloses a method for synthesizing chiral sulfonamide. In the method, chiral thiosulfinate is taken as a raw material and reduced with liquid ammonia containing lithium amide to obtain the chiral sulfonamide, and a reaction formula is as above, wherein, R is one of C1-C10 alkyl, phenyl, p-cresyl, o-cresyl, metal-cresyl, p-ethyl benzyl, p-tertiary-butyl phenyl, p-acetyl phenyl, o-acetyl phenyl and naphthyl. The method sequentially comprises the following steps: preparing the lithium amide; dropwise adding the lithium amide to chiral thiosulfinate solution and stirring for reaction; and adding ice to obtained mixture after the reaction, extracting, combining organic phases and eliminating solvents, and crystallizing to obtain the chiral sulfonamide. The method has the advantages that synthesis cost is reduced by an oxidation method in the presence of a chiral catalyst; a ligand is a condensation product of cheap and available chloromycetin derivative and salicylaldehyde derivative; and reaction steps are less, the reaction conditions are mild and post-treatment is simple.

The invention discloses a synthetic method of bortezomib, which comprises the following steps of: taking isovaleraldehyde as an initial raw material, taking (R)-methylpropane-2-sulfinamide as a chiral reagent, generating (R,E)-2-methyl-N-(3-methyl butylidene) propane-2-sulfinamide by a condensation and dehydration reaction, then carrying out a nucleophilic addition reaction with pinacol diboron so as to generate (R)-1-N-methylpropane sulfinyl-3-methyl butane-1-pinacol borate ester, afterwards hydrolyzing under an acidic condition so as to obtain pinacol-(R)-1-amino-3-methyl butane-1-borate ester hydrochloride, then reacting with (S)-3-phenyl-2-(pyrazine-2-formamido) propionic acid under the existence of a coupling agent and also hydrolyzing under the action of isobutyl borate so as to generate a final product of the bortezomib. According to the synthetic method of the bortezomib, the (R)-methylpropane-2-sulfinamide which is easy to obtain is used as the chiral induction reagent, so that an obtained intermediate enantiomorph has higher purity, and a bulk drug which is finally obtained has better quality.

There is provided a cyanoacrylate composition comprising:

• • a cyanoacrylate; and
  • a 2-substituted benzothiazole or a derivative thereof

wherein the 2-substituent is an alkyl, an alkene, an alkylbenzyl, an alkylamino, an alkoxy, an alkylhydroxy, an ether, a sulfenamide, a thioalkyl or a thioalkoxy group, with the proviso that an amide portion of the sulfenamide does not have a tert butylamino or a morpholine group.

The invention relates to a sitagliptin chiral intermediate and an asymmetric synthesis method thereof. The asymmetric synthesis method comprises the steps: with 2,4,5-trifluorophenyl acetic acid as a starting material, carrying out a reduction reaction to obtain 2-(2,4,5-trifluorophenyl)ethanol, then carrying out a reaction with an oxidant, carrying out condensation of the product without separation and (R)-(+)-tert-butyl sulfinamide to obtain corresponding acetal, carrying out a reaction of the obtained product with dialkyl malonate to obtain a key chiral intermediate, hydrolyzing to obtain a corresponding organic amine, carrying out a reaction of the amine with caustic alkali and then acidifying to obtain a corresponding carboxylic acid, then carrying out condensation with 3-(trifluoromethyl)-5,6,7,8- tetrahydro-[1,2,4] triazolo[4,3-a]pyrazine hydrochloride to obtain sitagliptin tert-butyl oxanamide, and finally deprotecting with hydrochloric acid to obtain sitagliptin. The yields of all the steps are all higher, the used reagents are all conventional cheap reagents, no expensive chiral catalysts are used, the reaction conditions are quite mild, and the asymmetric synthesis method is suitable for industrialization.

The preparation method for a low temperature detachable anaerobic glum overcomes the poor maintainability, hard assembly to non-resistance heat material and part and depressed reliability, and comprises: A. by weight share, mixing 50-95 methyl dimethacrylate and 0.01-2 stabilizer to dissolve at 45-55Deg; B. adding 0.1-5 accelerant and 0.1-5 o-benzene sulfinamide; C. adding 10-15 unsaturated polyester, 5-50 modifier and 0.1-5 gas-phase SiO2 into the product in B, and cooling to room temperature; D. adding 1-10 oxide to stir evenly. This invention has little effect to adhesive strength and high benefit with low cost.

The invention relates to a method for synthesizing cyclic sulphoxide imine, sulfenamide and sulfamide by stereospecificty; the method comprises the following steps of: under the condition of room temperature, sulphinyl imine 4 and benzyne precursor 5 have reaction for 1-15h under the initiation of organic solvent and CsF, the cyclic sulphoxide imine 1 is generated; when the cyclic sulphoxide imine1 contains sulfonyl, the sulfonyl inside a molecule can be successfully removed under the condition of Mg/HOAc/AcONaDMF/H2O, and the cyclic sulphoxide imine 1 is obtained; under the condition of HCl(dioxane), the cyclic sulphoxide imine 1 is successfully transformed into the cyclic sulfenamide 2; and after the cyclic sulfenamide 2 is oxidized by m CPBA, the cyclic sulfamide 3 is obtained. The method has the characteristics of low cost, high yield, mild reaction condition, environmental protection, good repeatability and the like.

Belonging to the field of organic synthesis, the invention provides an alpha-fluoroalkyl-alpha-amino acid compound containing a tetrasubstituted carbon chiral center, and also discloses a preparation method of the compound. The method utilizes cheap and easily available fluoroalkyl-containing unsaturated ketone and chiral prosthetic group sulfinamide as the starting raw material, and by means of preparation of alpha, beta-unsaturated fluoroalkyl sulfenyl ketoimine, selective addition of an organic metallic reagent and chiral alpha, beta-unsaturated imine, removal of chiral prosthetic group, protection of amino group, and finally double-bond simple oxidation in order, the alpha-fluoroalkyl-alpha-amino acid compound containing the tetrasubstituted carbon chiral center can be obtained by entiomeric purity. The method provided by the invention has the advantages of cheap and easily available raw materials, simple operation of the synthesis method, good selectivity, high yield, and reaction with universal applicability, is a universal method for synthesis of the alpha-fluoroalkyl-alpha-amino acid compound containing the tetrasubstituted carbon chiral center, and has very good application prospects.

The invention relates to a method for synthetizing an organic compound. A process method for synthetizing tert-butyl sulfinamide comprises the following steps: (a) under the temperature of between 50 DEG C below zero to 70 DEG C below zero, adding triphenyl methyl halide into liquid ammonia to obtain N methyl triphenyl ammonia; (b) under the temperature of between 60 DEG C below zero and 70 DEG Cbelow zero, adding n-butyl lithium into organic solution of N methyl triphenyl ammonia to obtain organic solution of N methyl (triphenyl) lithium amide; (c) at the temperature of between 50 DEG C below zero and 70 DEG C below zero, dropwise adding organic solution of (S)-tert-butyl sulfinic acid tert-butyl thioester into the N-methyl (triphenyl) lithium amide, quenching the mixture by using water, carrying out deodorization by using dimethyl sulfate, destroying excessive dimethyl sulfate by using ammonia and carrying out post treatment to obtain (S)-N-methyl (triphenyl) tert-butyl sulfinamide; and (d) taking the product in the step (c), adding dilute acid into the product, adjusting the pH value of the mixture to 3, neutralizing the mixture by using alkaline solution until the pH value isbetween 13 and 14 and carrying out post treatment to obtain (S)-tert-butyl sulfinamide. The process method for synthetizing the tert-butyl sulfinamide has simple and convenient operation and good process stability, avoids copious cooling at the low or ultralow temperature, reduces the using amount of ammonia, removes foul odour and is easy to realize industrial production.

The invention discloses a method for preparing pure enantio-methylpropane-2-sulfinamide. The method comprises the following steps: carrying out selective oxidation on di-tert-butyl disulfide and hydrogen peroxide, reacting with an acylation reagent so as to obtain tert-butylsulfinyl chloride and tertiary butyl sulfonyl bromide, further reacting with hydrazine hydrate so as to obtain tertiary butylhydrazide, further carrying out resolution and separation with a DBTA resolving agent, and carrying out cracking with zinc acetate, thereby obtaining the pure enantio-methylpropane-2-sulfinamide. Themethod is simple, convenient and stable in process operation, high in yield and good in environment protection, and compared with a conventional process, the method is cheap and easy in raw materialobtaining, low in production cost of pure enantio-methylpropane-2-sulfinamide, and beneficial to industrial on-scale production.

The invention provides a method for asymmetrically synthesizing (S)-nicotine. The method comprises the following steps: condensing 3-pyridylaldehyde and (R)-tert-butanesulfinamide to obtain chiral imine; adding ethyl acetoacetate to react with the chiral imine to obtain chiral amine; removing tert-butyl sulfinyl and ester group from the chiral amine to obtain chiral aminoketone; protecting the amino group of the chiral aminoketone by using phthalic anhydride; adding a brominating agent to brominate the chiral aminoketone to obtain bromide; and adding hydrazine hydrate to remove a Pht protecting group and form a tetrahydropyrrole ring at the same time by utilizing a one-pot method, reducing carbonyl into methylene to obtain (S)-nornicotine, and carrying out N-methylation on the (S)-nornicotine to obtain the final product (S)-nicotine. According to the method, direct construction of chiral carbon is realized by utilizing a cheap chiral reagent (R)-tert-butanesulfinamide, (S)-nicotine with high chiral purity is obtained at a relatively high yield through subsequent simple reaction steps, and the method is simple, convenient, feasible and suitable for industrial production.

The invention discloses a large-scale preparation method of a chiral sulfinamide monophosphine ligand. The method includes condensing chiral sulfinamide and 2-(diphenylphosphino)benzaldehyde which areadopted as raw materials to obtain an intermediate that is chiral sulfinyl imide, and carrying out a nucleophilic addition reaction with a phenylmagnesium bromide reagent to generate the chiral sulfinamide monophosphine ligand. The intermediate imine product and a final product chiral sulfinamide monophosphine ligand are purified by adopting a crystallization method, and column chromatography isnot needed. The method has the characteristics of cheap and accessible raw materials, simple synthesis steps, large-scale synthesis and preparation, a specific three-dimensional structure of the product and the like. The method is mild in condition, and is of important significance for future process and commercialization development of chiral sulfinamide monophosphine ligand products.

Covalent, irreversible small-molecule inhibitors that modify the sulfenyl form (i.e., sulfenic acid, RSOH and sulfenamide, RSNR′2) of therapeutically important proteins (particularly kinases and phosphatases) are disclosed, where the compositions include a compound having a substituted aryl or heterocyclic core structure that promotes binding interactions with a specific protein, and a nucleophilic reaction center (carbon, nitrogen, sulfur, or phosphorous) that is capable of forming a covalent bond with a sulfenic acid- or sulfenamide-modified cysteine residue in the protein. Methods for synthesizing these compounds are also disclosed, as well as methods of using them for determining the bioactivity of a chemical composition comprising an active compound toward a specific protein and for determining the potency of an inhibitor against a specific protein.