Methods of synthesizing substituted tetracycline compounds are provided.

The present invention relates to a 5-step process for preparing iosimenol starting from ammonium 3-amino-5-(aminocarbonyl)benzoate which is first converted to 3-amino-5-(aminocarbonyl)-2,4,6-triiodobenzoic acid using sodium iodine dichloride (NaICl.sub.2). The present invention further relates to processes for purifying iosimenol.

The present invention relates to a 5-step process for preparing iosimenol starting from ammonium 3-amino-5-(aminocarbonyl)benzoate which is first converted to 3-amino-5-(aminocarbonyl)-2,4,6-triiodobenzoic acid using sodium iodine dichloride (NaICl.sub.2). The present invention further relates to processes for purifying iosimenol.

The filter medium is a filter medium which uses a liquid containing oil and water as a separation target, and has a channel for the liquid. The filter medium includes a base constituting the channel, and one or more of nitrogen-containing fluorine compounds which are provided on at least a portion of a surface of the channel. The nitrogen-containing fluorine compound includes an oil-repellency imparting group and any one hydrophilicity imparting group selected from a group consisting of an anion type, a cation type, and an amphoteric type, in a molecule.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

A process for the preparation of a compound of formula (I) and of a acid salt (T) wherein R.sup.1 is selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R.sup.2 and R.sup.3, are, independently of each other, selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, are independently of each other, selected from the group consisting of H, alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, and wherein the acid salt is a 2,3-Ditoluoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid salt, 2,3-Dianisoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid mono(dimethylamide) salt or a mixture of two or more thereof, wherein the tartaric acid salt (T) of the compound of formula (I) contains at least 90% by weight of the tartaric salt of the compound of formula (Ia) based on the total weight of the acid salt of the compound of formula (I).

##STR00001##

A process for the preparation of a compound of formula (I) and of a acid salt (T) wherein R.sup.1 is selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R.sup.2 and R.sup.3, are, independently of each other, selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, are independently of each other, selected from the group consisting of H, alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, and wherein the acid salt is a 2,3-Ditoluoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid salt, 2,3-Dianisoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid mono(dimethylamide) salt or a mixture of two or more thereof, wherein the tartaric acid salt (T) of the compound of formula (I) contains at least 90% by weight of the tartaric salt of the compound of formula (Ia) based on the total weight of the acid salt of the compound of formula (I).

##STR00001##

Provided is a method for preparing L-glufosinate from an L-homoserine derivative compound, the method including a step (step a) of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1, and a step (step b) of preparing a compound of Chemical Formula 3 from the compound of Chemical Formula 2.