3-OXO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID METHYL ESTER

Base Information

• Chemical Name: 3-OXO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID METHYL ESTER
• CAS No.: 769195-26-8
• Molecular Formula: C11H9F3O3
• Molecular Weight: 246.186
• Hs Code.: 2918300090
• Mol file: 769195-26-8.mol

Synonyms:methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

Chemical Property of 3-OXO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID METHYL ESTER

Chemical Property:

• Melting Point: 40-41 °C
• Refractive Index: 1.469
• Boiling Point: 273.265 °C at 760 mmHg
• PKA: 9.95±0.46(Predicted)
• Flash Point: 115.458 °C
• PSA: 43.37000
• Density: 1.331 g/cm³
• LogP: 1.77860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

Methyl3-Oxo-4-(2,4,5-trifluorophenyl)butanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 3-Oxo-4-(2,4,5-trifluorophenyl)butanoate is a useful synthetic intermediate in the synthesis of Sitagliptin (S491000); a trizolopyrazine dipeptidyl peptidase (DPP) IV inhibitor for the treatment of type II diabetes.

Technology Process of 3-OXO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID METHYL ESTER

There total 9 articles about 3-OXO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID METHYL ESTER 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: 91.0%

2-(2,4,5-trifluorophenyl)acetyl chloride (1176895-65-0) + bromoacetic acid methyl ester (96-32-2) → 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (769195-26-8)

Guidance literature:

bromoacetic acid methyl ester; With iodine; magnesium; In tetrahydrofuran; at 45 - 50 ℃; Inert atmosphere;

2-(2,4,5-trifluorophenyl)acetyl chloride; With copper(l) iodide; In tetrahydrofuran; at -20 - 5 ℃; Inert atmosphere;

Reference yield: 88.7%

methanol (67-56-1) + 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (764667-64-3) → 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (769195-26-8)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1016/j.bmcl.2007.01.111

Reference yield: 85.0%

5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (764667-64-3) → 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (769195-26-8)

Guidance literature:

With methanol; at 60 - 63 ℃;

upstream raw materials:

monomethyl monopotassium malonate

(2,4,5-trifluorophenyl)acetic acid

methanol

5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Downstream raw materials:

(2Z)-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester

(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

(R)-[3-oxo-3-pyrazolidin-1-yl-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

Refernces

• 1、 -. "SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF". Paragraph 0156; 0157; 0158; 0159; 0160. . Retrieved 2013/06/28.
• 2、 -. "SITAGLIPTIN SYNTHESIS". Page/Page column 9. . Retrieved 2012/05/07.