PF-04971729

Base Information

• Chemical Name: PF-04971729
• CAS No.: 1210344-57-2
• Molecular Formula: C22H25ClO7
• Molecular Weight: 436.889
• Mol file: 1210344-57-2.mol

Synonyms:PF 04971729-00; 1,6-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-beta-L-idopyranose; (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; cc-212

Chemical Property of PF-04971729

Chemical Property:

• Boiling Point: 630.5±55.0 °C(Predicted)
• PKA: 12.95±0.70(Predicted)
• PSA: 108.61000
• Density: 1.455
• LogP: 1.35650
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ertugliflozin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Composition and Structure: Ertugliflozin is a selective inhibitor of sodium-glucose cotransporter 2 (SGLT2), with a chemical structure 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. In commercial formulation, it is available as a cocrystal with L-pyroglutamic acid (ertugliflozin?L-PGA).
• Uses and Mechanism of Action: Approved by the Food and Drug Administration (FDA) in the United States and other regulatory authorities for the improvement of glycemic control in adults with type 2 diabetes mellitus (T2DM). Available in 5 mg and 15 mg strengths as immediate-release tablets for oral administration. Besides glucose lowering, it induces natriuresis, contributing to blood pressure reduction and beneficial effects on kidney function.^[1]
• Pharmacokinetics: Rapid oral absorption with peak plasma concentrations reached within 1-2 hours post-dose. Once-daily dosing achieves steady-state concentrations by 6 days. Metabolized primarily via glucuronidation and excreted minimally by the kidneys.^[2]
• Regulatory Status: Approved by regulatory agencies such as the FDA and EMA for the treatment of T2DM.
• References: [1] Cardiovascular Outcomes with Ertugliflozin in Type 2 Diabetes; DOI 10.1056/NEJMoa2004967; [2] Overview of the Clinical Pharmacology of Ertugliflozin, a Novel Sodium-Glucose Cotransporter 2 (SGLT2) Inhibitor; DOI 10.1007/s40262-020-00875-1

Technology Process of PF-04971729

There total 58 articles about PF-04971729 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: 92.0%

C28H35ClO8 → Ertugliflozin (1210344-57-2)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; for 1h;

Reference yield: 91.4%

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol → Ertugliflozin (1210344-57-2)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; water; at 30 ℃; for 8h;

Reference yield: 89.0%

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]methanol → Ertugliflozin (1210344-57-2)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 3h;

upstream raw materials:

{(2S,3S)-3,4,5-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6,8-dioxa-bicyclo[3.2.1]oct-1-yl}-methanol

C₂₈H₃₇ClO₇S₂

(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

(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

Downstream raw materials:

C₅₀H₃₇ClN₄O₁₉

((1R,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)-phenyl)-2,3,4-trihydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl)methyl acetate

(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

(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

Refernces

• 1、 -. "AN IMPROVED PURIFICATION PROCESS FOR THE PREPARATION OF ERTUGLIFLOZIN AND ERTUGLIFLOZIN L-PYROGLUTAMIC ACID CO-CRYSTAL". Page/Page column 18; 17. . Retrieved 2022/01/04.
• 2、 -. "A NOVEL PROCESS FOR THE PREPARATION OF SGLT-2 INHIBITORS". Page/Page column 21. . Retrieved 2020/01/24.