Abstract

The invention relates to a continuous method for the production of a chemical compound A, comprising: – provision of a mixture comprising the chemical compound A and a chemical compound B which is an atropisomer of the chemical compound A; – chromatographic separation of the mixture so as to collect a fraction rich in chemical compound A and a fraction rich in chemical compound B; – a racemisation treatment of the fraction rich in chemical compound B, in which the chemical compound B is partially converted into chemical compound A, so as to obtain a racemised fraction; – recycling of the racemised fraction to the step of chromatographic separation of the mixture. The invention also relates to a plant for implementing this method.

IPC Classes  ?

• C07B 55/00 - RacemisationComplete or partial inversion
• C07B 57/00 - Separation of optically-active organic compounds
• C07D 239/91 - Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3

Abstract

The invention relates to compounds of formula (Formula III) (III) and of formula (Formula (IV) (IV), to methods for producing said compounds, and to the use thereof in the synthesis of saxagliptin.

IPC Classes  ?

• C07C 67/39 - Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
• C07C 315/04 - Preparation of sulfonesPreparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
• C07C 317/24 - SulfonesSulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
• C07C 51/09 - Preparation of carboxylic acids or their salts, halides, or anhydrides from carboxylic acid esters or lactones
• C07C 59/215 - Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen-containing groups
• C07C 209/52 - Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers

Abstract

The invention relates to a method for producing a compound of formula (I) wherein R is selected from the groups comprising hydroxy, amino, and C1-C6 alkoxy or a salt thereof. Said method comprises a step of solvolysis of adamantoyl cyanide of formula (II). The aim of the invention is to provide an alternative synthetic pathway, based on simple and robust synthesis steps.

IPC Classes  ?

• C07C 51/06 - Preparation of carboxylic acids or their salts, halides, or anhydrides from carboxylic acid amides
• C07C 51/08 - Preparation of carboxylic acids or their salts, halides, or anhydrides from nitriles
• C07C 59/353 - Saturated compounds having more than one carboxyl group containing keto groups containing rings
• C07C 67/20 - Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
• C07C 231/06 - Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
• C07C 253/14 - Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
• C07C 69/00 - Esters of carboxylic acidsEsters of carbonic or haloformic acids

Abstract

Method for producing fenofibrate from fenofibric acid by in situ preparation of fenofibric acid chloride by means of the action of a chlorinating agent on the acid then by reaction with isopropanol without isolation of the acid chloride.

IPC Classes  ?

• C07C 67/14 - Preparation of carboxylic acid esters from carboxylic acid halides
• C07C 69/712 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Abstract

Process for preparing 2-(n-butyl)-5-nitrobenzofuran of formula (I) from 1-fluoro-4-nitrobenzene, characterized in that 1-hexyn-3-ol is reacted, and then the product obtained is subjected to Claisen rearrangement and to intramolecular cyclization.

IPC Classes  ?

• C07D 307/79 - Benzo [b] furansHydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Abstract

The invention relates to a method for preparing 2-(n-butyl)-5-nitrobenzofuran from 1-halogeno-4-nitrobenzene, characterised in that it comprises reacting the 1-hexen-3-ol, then subjecting the product to a Claisen rearrangement, followed by a catalytic intramolecular cyclisation.

IPC Classes  ?

• C07C 205/22 - Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro group bound to the ring
• C07D 307/79 - Benzo [b] furansHydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Abstract

The invention relates to a method for preparing 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane from 4-nitrophenol, that comprises preparing a 2-iodo-(or 2-bromo)-4-nitrophenol derivative, carrying out a Sonogashira coupling reaction by the hexyne action, followed by a Pacylation by a reactive derivative of methoxybenzoic acid and the demethylation of the 4-méthoxybenzoic derivative thus obtained.

IPC Classes  ?

• C07D 307/82 - Benzo [b] furansHydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring