The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

##STR00001##

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

##STR00001##

The subject matter disclosed herein is directed to novel She inhibitors of Formula (II). These compounds are useful for treating impaired insulin sensitivity, glucose tolerance, obesity, diabetes, metabolic syndrome, NAFLD, NASH, PSC, PBC, or other metabolic syndrome component conditions.

##STR00001##

Provided are compounds and salts having a structure of Formula (I) or (II): (I), and (II) wherein: both of the chiral carbon atoms denoted by “*” are both in the R configuration or both in the S configuration. Compounds and salts of Formulae (I) and (II) are useful in the preparation of enantiomerically pure amino acids. Conversion of amino acids to D-form from any of L-form, racemate or other enantiomerically impure mixtures or conversion of amino acids to L-form from any of D-form, racemate or other enantiomerically impure mixtures is disclosed.

##STR00001##

A process A for the production of compounds of formula I is provided. ##STR00001## Process A includes Step A of reacting compounds of formula II ##STR00002##
with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. A process B for the production of compounds of formula III is also provided. ##STR00003## Process B includes Step B of reacting compounds of formula I with Br.sub.2 in the presence of DIPEA. A process C for the production of compounds of formula IV is further provided. ##STR00004## Process C includes Step C of reacting compounds of formula III with di(C.sub.1-C.sub.4-alkoxy)methane and either POCl.sub.3, or a mixture comprising POCl.sub.3 and DMF, in the presence of DIPEA. Additionally, the use of DIPEA as a base in the production of compounds of formula I, compounds of formula III, or compounds of formula IV is provided.

A process A for the production of compounds of formula I is provided. ##STR00001## Process A includes Step A of reacting compounds of formula II ##STR00002##
with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. A process B for the production of compounds of formula III is also provided. ##STR00003## Process B includes Step B of reacting compounds of formula I with Br.sub.2 in the presence of DIPEA. A process C for the production of compounds of formula IV is further provided. ##STR00004## Process C includes Step C of reacting compounds of formula III with di(C.sub.1-C.sub.4-alkoxy)methane and either POCl.sub.3, or a mixture comprising POCl.sub.3 and DMF, in the presence of DIPEA. Additionally, the use of DIPEA as a base in the production of compounds of formula I, compounds of formula III, or compounds of formula IV is provided.

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction. ##STR00001##

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction. ##STR00001##

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

##STR00001##

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

##STR00001##