Ertugliflozin

Base Information

• Chemical Name: Ertugliflozin
• CAS No.: 1210344-83-4
• Molecular Formula: C27H32ClNO10
• Molecular Weight: 566.005
• Mol file: 1210344-83-4.mol

Synonyms:ertugliflozin-L-pyroglutamic acid;(1S,2S,3S,4R,55)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-hydroxymethyl-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol pyroglutamic acid;cocrystal of (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 and L-pyroglutamic acid;

Chemical Property of Ertugliflozin

Chemical Property:

• Melting Point: 142.5 °C
• PSA: 175.01000
• LogP: 1.03490
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

ErtugliflozinL-pyroglutamicAcid(1:1) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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.

Technology Process of Ertugliflozin

There total 12 articles about Ertugliflozin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.3%

Ertugliflozin (1210344-57-2) + L-Pyroglutamic acid (98-79-3) → (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 (1210344-83-4)

Guidance literature:

Ertugliflozin; In methanol; water; isopropyl alcohol; at 40 - 60 ℃; under 30 Torr;

L-Pyroglutamic acid; In methanol; water; isopropyl alcohol; at 40 - 80 ℃;

DOI:10.1021/op4002802

Reference yield:

(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 (1629222-50-9) → (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 (1210344-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 5%-palladium/activated carbon; hydrogenchloride; hydrogen / toluene; methanol; water / 18 h / 25 °C / 2585.81 Torr / Inert atmosphere

2.1: methanol; water; isopropyl alcohol / 40 - 60 °C / 30 Torr

2.2: 40 - 80 °C

With hydrogenchloride; 5%-palladium/activated carbon; hydrogen; In methanol; water; isopropyl alcohol; toluene;

DOI:10.1021/op4002802

Reference yield:

(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 (1298086-18-6) → (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 (1210344-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 0.25 h / 20 °C

2.1: methanol; water; isopropyl alcohol / 40 - 60 °C / 30 Torr

2.2: 40 - 80 °C

With sodium methylate; In methanol; water; isopropyl alcohol;

DOI:10.1021/op4002802

upstream raw materials:

(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

Ertugliflozin

L-Pyroglutamic acid

(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

Refernces

• 1、 -. "SOLID FORMS OF ERTUGLIFLOZIN FREE BASE AND SOLID DISPERSIONS COMPRISING ERTUGLIFLOZIN L-PYROGLUTAMIC ACID.". Page/Page column 17. . Retrieved 2020/02/23.
• 2、 -. "ERTUGLIFLOZIN CO-CRYSTALS AND PROCESS FOR THEIR PREPARATION". Page/Page column 8; 9. . Retrieved 2016/12/22.