Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate

Base Information

• Chemical Name: Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate
• CAS No.: 1234321-81-3
• Molecular Formula: C13H12F3NO3
• Molecular Weight: 287.238
• Mol file: 1234321-81-3.mol

Synonyms:Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate;(Z)-methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate;(2Z)-3-(Acetylamino)-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester

Chemical Property of Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate

Chemical Property:

• Boiling Point: 436.6±45.0 °C(Predicted)
• PKA: 13.58±0.46(Predicted)
• PSA: 58.89000
• Density: 1.304±0.06 g/cm3(Predicted)
• LogP: 2.67970
• Storage Temp.: 2-8°C

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

(Z)-Methyl3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate

There total 5 articles about Methyl 3-acetamido-4-(2,4,5-trifluorophenyl)but-2-enoate 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: 79.0%

(2Z)-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester (881995-70-6) + acetic anhydride (108-24-7) → (Z)-3-acetylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester (1234321-81-3)

Guidance literature:

With pyridine; In tetrahydrofuran; for 20h; Reflux;

Reference yield: 61.0%

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (769195-26-8) + acetamide (60-35-5) → (Z)-3-acetylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester (1234321-81-3)

Guidance literature:

With diphenylammonium trifluoromethanesulfonate; In toluene; for 8h; stereoselective reaction; Reflux; Green chemistry;

DOI:10.1007/s11696-019-00838-2

Reference yield: 47.0%

methanol (67-56-1) + ammonium acetate (631-61-8,92206-38-7) + 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (764667-64-3) → (Z)-3-acetylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester (1234321-81-3)

Guidance literature:

methanol; 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione; In toluene; at 60 - 120 ℃; for 72h;

ammonium acetate; With ammonium hydroxide; at 25 - 60 ℃; for 24h;

upstream raw materials:

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

acetic anhydride

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester

acetamide

Downstream raw materials:

(R)-methyl-3-N-acetylamino-4-(2,4,5-trifluorophenyl)butanoate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

sitagliptin

Refernces

• 1、 -. "Recycling method of acetyl Meldrum's acid derivative degradation waste". Paragraph 0056-0061; 0065-0067. . Retrieved 2021/07/01.
• 2、 -. "PROCESS AND INTERMEDIATES FOR THE PREPARATION OF N-ACYLATED-4-ARYL BETA-AMINO ACID DERIVATIVES". Page/Page column 20. . Retrieved 2010/08/04.