(Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE

Base Information

• Chemical Name: (Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE
• CAS No.: 112811-70-8
• Molecular Formula: C16H16F3NO4
• Molecular Weight: 343.303
• Mol file: 112811-70-8.mol

Synonyms:(Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE;2-(2,4,5-Trifluoro-3-Methoxybenzoyl)-3-cyclopropylaMinoacrylic Acid Ethyl Ester;Ethyl 2-(2,4,5-trifluoro-3-methoxybenzoyl)-3-cyclopropylaminoacrylate

Chemical Property of (Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE

Chemical Property:

• Boiling Point: 463.2±45.0 °C(Predicted)
• PKA: 2.70±0.70(Predicted)
• PSA: 64.63000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 2.88510

Purity/Quality:

99% ^*data from raw suppliers

2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-cyclopropylaminoacrylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-cyclopropylaminoacrylic Acid Ethyl Ester is used in the preparation Gatifloxacin (G250000) and key intermediates for the synthesis third-generation fluoroquinolone antibiotics.

Technology Process of (Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE

There total 14 articles about (Z)-ETHYL 3-(CYCLOPROPYLAMINO)-2-(2,4,5-TRIFLUORO-3-METHOXYBENZOYL)ACRYLATE 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:

Cyclopropylamine (765-30-0) + ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (122375-85-3) → ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (112811-70-8)

Guidance literature:

at 0 ℃;

DOI:10.1016/j.bmc.2007.11.050

Reference yield:

C15H18F3NO4 + Cyclopropylamine (765-30-0) → ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (112811-70-8)

Guidance literature:

In toluene; at 30 - 45 ℃; for 2h; Temperature;

Reference yield:

2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (112811-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.88 g / Et₃N / toluene / 5 h / 90 °C

2: ethanol; diethyl ether / 3 h / 20 °C

With triethylamine; In diethyl ether; ethanol; toluene;

DOI:10.1016/j.ejmech.2006.07.003

upstream raw materials:

Cyclopropylamine

(Z)-3-Diethylamino-2-(2,4,5-trifluoro-3-methoxy-benzoyl)-acrylic acid ethyl ester

ethyl α(E)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate

3-methoxy-2,4,5-trifluorobenzoic acid

Downstream raw materials:

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

moxifloxacin

moxifloxacin hydrochloride

1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-amino-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Refernces

• 1、 Gomez, Catherine,Ponien, Prishila,Serradji, Nawal,Lamouri, Aazdine,Pantel, Alix,Capton, Estelle,Jarlier, Vincent,Anquetin, Guillaume,Aubry, Alexandra. "Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis". . p. 948 - 956. Retrieved 2013/03/13.
• 2、 Anquetin, Guillaume,Greiner, Jacques,Mahmoudi, Nassira,Santillana-Hayat, Maud,Gozalbes, Rafael,Farhati, Khemais,Derouin, Francis,Aubry, Alexandra,Cambau, Emmanuelle,Vierling, Pierre. "Design, synthesis and activity against Toxoplasma gondii, Plasmodium spp., and Mycobacterium tuberculosis of new 6-fluoroquinolones". . p. 1478 - 1493. Retrieved 2007/10/03.