1210344-83-4

Basic information

• Product Name: Ertugliflozin
• Synonyms: Pidolate;ERTUGLIFLOZIN PIDOLATE;Gliadine L- pyroglutamate;PF-04971729 L-pyroglutamic acid;Ertugliflozin L-pyroglutamic Acid (1:1);PF-04971729 ((S)-5-oxopyrrolidine-2-carboxylic acid);(S)-5-Oxopyrrolidine-2-carboxylic acid compound with (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1);(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid
• CAS NO: 1210344-83-4
• Molecular Formula: C₅H₇NO₃*C₂₂H₂₅ClO₇
• Molecular Weight: 565.99668
• Mol File: 1210344-83-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Ertugliflozin(CAS DataBase Reference)
• NIST Chemistry Reference: Ertugliflozin(1210344-83-4)
• EPA Substance Registry System: Ertugliflozin(1210344-83-4)

Safety Data

• Hazardous Substances Data: 1210344-83-4(Hazardous Substances Data)

Usage

Uses

Ertugliflozin L-pyroglutamic Acid is a reagent in the synthesis of Ertugliflozin (1210344-57-2) a sodium/glucose cotransporter 2 (SGLT2) inhibitor used to treat type 2 diabetes.

Upstream product

• 1528636-29-4 ((2R,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-yl)methanol 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 714269-57-5 (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 
• 1528636-39-6 (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1528636-33-0 (2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde 
• 1431329-05-3 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one 
• 1431329-06-4 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate 
• 1298086-18-6 (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate 
• 1210344-57-2 Ertugliflozin 
• 98-79-3 L-Pyroglutamic acid 
• 1629222-50-9 (2S,3S,4R)-2,3,4-tris(benzyloxy)-1-((benzyloxy)-methyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane 

Relevant articles and documents

AN EFFICIENT PROCESS FOR THE PREPARATION OF ERTUGLIFLOZIN L-PYROGLUTAMIC ACID AND INTERMEDIATES THEREOF

The present invention relates to an efficient process for the preparation of Ertugliflozin L-pyroglutamic acid of formula (I) and intermediate thereof, in environment friendly conditions. The present invention further relates to a process for the preparation of substantially pure intermediate of formula (IV).

Preparation method of ertugliflozin and intermediate of ertugliflozin

The invention provides a synthesis method of ertugliflozin. The route relates to a new intermediate compound 3 and a compound 5, an SGLT-2 inhibitor ertugliflozin is prepared by virtue of the new intermediate compound 3 and the compound 5, and the preparation method is simple in process route, low in cost and applicable to industrial production. (The compound 3 and the compound 5 are described in the specification.).

Commercial route research and development for SGLT2 inhibitor candidate ertugliflozin

A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[ 3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.