A process for preparation of pyrroles having hypolipidemic hypocholesteremic activities

A process for the preparation of saroglitazar magnesium of Formula (I),

• the process comprising:
• (a) reacting hydroxy compound (A) with a mesylate compound (A1) in one or more organic solvents in the presence of a base and a phase transfer catalyst to obtain alkoxy ester compound of Formula (II);
• (b) hydrolyzing the alkoxy ester compound of Formula (II) with a base to obtain saroglitazar;
• and
• (c) reacting the saroglitazar with a magnesium source to obtain saroglitazar magnesium of Formula (I).

A process for the preparation of saroglitazar of Formula (IA) or its pharmaceutically acceptable salt,

• the process comprising:
• (a) reacting hydroxy compound (A) with a compound of Formula (A1′) in one or more organic solvents in the presence of a base and a phase transfer catalyst to obtain alkoxy ester compound of Formula (II),
• wherein, R is mesylate, tosylate, or triflate;
• (b) hydrolyzing the alkoxy ester compound of Formula (II) with a base to obtain saroglitazar;
• and
• (c) optionally, converting the saroglitazar to its pharmaceutically acceptable salt.

A process for the preparation of hydroxy compound of Formula (A),

• the process comprising:
• (a) reacting L-tyrosine (E) with cupric sulphate pentahydrate in the presence of a base to obtain copper complex of L-tyrosine;
• (b) reacting the copper complex of L-tyrosine with benzyl halide in the presence of a base, followed by hydrolysis to obtain compound (D);
• (c) diazotization of the compound (D) in the presence of sodium nitrite and an acid followed by hydrolysis with water to obtain compound (C);
• (d) reacting the compound (C) with diethyl sulfate in one or more organic solvents in the presence of a base and a phase transfer catalyst to obtain compound (B);
• and
• (e) deprotecting the compound (B) to obtain the hydroxy compound (A).

A process for the preparation of mesylate compound of Formula (A1),

• the process comprising:
• (a) reacting 2-bromo-1-(4-(methylthio)phenyl)ethanone (E1) with methyl acetoacetate in one or more organic solvents in the presence of a base to obtain compound (D1);
• (b) hydrolyzing the compound (D1) with a base followed by decarboxylation to obtain compound (C1);
• (c) reacting the compound (C1) with ethanolamine under Paal-Knorr conditions in the presence of an acid to obtain compound (B1);
• and
• (d) reacting the compound (B1) with methane sulphonyl chloride in the presence of a base in one or more organic solvents to obtain the mesylate compound (A1).