Tafluprost ethyl amide

Base Information

• Chemical Name: Tafluprost ethyl amide
• CAS No.: 1185851-52-8
• Molecular Formula: C24H33F2NO4
• Molecular Weight: 437.52
• Mol file: 1185851-52-8.mol

Synonyms:Tafluprost ethyl amide;Dechloro dihydroxy difluoro ethylcloprostenolamide

Chemical Property of Tafluprost ethyl amide

Chemical Property:

• Boiling Point: 609.3±55.0 °C(Predicted)
• PKA: 14.48±0.70(Predicted)
• PSA: 78.79000
• Density: 1.191±0.06 g/cm3(Predicted)
• LogP: 4.25840

Purity/Quality:

99%min ^*data from raw suppliers

Tafluprost ethyl amide ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tafluprost ethyl amide

There total 17 articles about Tafluprost ethyl amide 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: 85.0%

ethylamine (75-04-7,85404-22-4) + tafluprost (209860-87-7) → (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide (1185851-52-8)

Guidance literature:

In water; at 20 ℃; for 60h;

DOI:10.3390/molecules22020217

Reference yield:

1-{(4Z)-6-[(1R,2R,3R,5S)-2-[(1E)-3-(tert-butyldimethylsilyloxy)-4-(phenoxy)but-1-enyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane → (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide (1185851-52-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3 h / 20 °C

2.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

3.1: camphor-10-sulfonic acid / dichloromethane; methanol / 7 h / 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

4.2: 0.5 h / 20 °C

5.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; tetrahydrofuran / 24.25 h / 0 °C / Inert atmosphere; Reflux

6.1: lithium hydroxide monohydrate / methanol

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 °C / Inert atmosphere

7.2: 21 h / 0 - 20 °C / Inert atmosphere

8.1: water / 60 h / 20 °C

With dmap; lithium hydroxide monohydrate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 2.1: |Julia-Lythgoe Olefination;

DOI:10.3390/molecules22020217

Reference yield:

1-{(Z)-6-[(1R,2R,3R,5S)-2-[3-(tert-butyldimethylsilyloxy)-4-phenoxy-1-(phenylsulfonyl)butyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo-[2.2.2]octane → (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide (1185851-52-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: disodium hydrogenphosphate; sodium amalgam / methanol; tetrahydrofuran / 17 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3 h / 20 °C

3.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

4.1: camphor-10-sulfonic acid / dichloromethane; methanol / 7 h / 20 °C

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5.2: 0.5 h / 20 °C

6.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; tetrahydrofuran / 24.25 h / 0 °C / Inert atmosphere; Reflux

7.1: lithium hydroxide monohydrate / methanol

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 0 °C / Inert atmosphere

8.2: 21 h / 0 - 20 °C / Inert atmosphere

9.1: water / 60 h / 20 °C

With dmap; disodium hydrogenphosphate; lithium hydroxide monohydrate; camphor-10-sulfonic acid; sodium amalgam; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 3.1: |Julia-Lythgoe Olefination;

DOI:10.3390/molecules22020217

upstream raw materials:

AFP-172

ethylamine

tafluprost

phenol