phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester

Base Information

• Chemical Name: phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester
• CAS No.: 1301696-56-9
• Molecular Formula: C₁₉H₃₃INO₅P
• Molecular Weight: 513.353
• Mol file: 1301696-56-9.mol

Synonyms:phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester

Chemical Property of phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester

There total 6 articles about phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] 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: 63.0%

phosphoric acid di-tert-butyl ester (S)-4-[2-(3-iodo-4-octylphenyl)ethyl]-2-oxooxazolidin-4-ylmethyl ester (1301696-49-0) → phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester (1301696-56-9)

Guidance literature:

phosphoric acid di-tert-butyl ester (S)-4-[2-(3-iodo-4-octylphenyl)ethyl]-2-oxooxazolidin-4-ylmethyl ester; With lithium hydroxide; In ethanol; water; at 20 - 60 ℃; for 68h;

With hydrogenchloride; water; In ethanol; at 20 ℃; for 1h;

With sodium hydroxide; In ethanol; water;

DOI:10.1002/cmdc.201000477

Reference yield:

fingolimod (162359-55-9) → phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester (1301696-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: iodine; silver trifluoromethanesulfonate; silver sulfate / dichloromethane / 18 h / 20 °C

2.1: sodium hydroxide / 20 °C

3.1: 1H-tetrazole / dichloromethane; tetrahydrofuran / 0 - 20 °C

3.2: 1.5 h / 20 °C

4.1: Chiralpak AS-PREP column / n-heptane; ethanol; methanol / Resolution of racemate

5.1: ethanol; lithium hydroxide / 68 h / 20 - 60 °C

5.2: 1 h / 20 °C

With 1H-tetrazole; ethanol; iodine; silver trifluoromethanesulfonate; silver sulfate; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane;

Reference yield:

2-amino-2-[2-(3-iodo-4-octylphenyl)ethyl]-1,3-propandiol (1301696-39-8) → phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(3-iodo-4-octylphenyl)butyl] ester (1301696-56-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / 20 °C

2.1: 1H-tetrazole / dichloromethane; tetrahydrofuran / 0 - 20 °C

2.2: 1.5 h / 20 °C

3.1: Chiralpak AS-PREP column / n-heptane; ethanol; methanol / Resolution of racemate

4.1: ethanol; lithium hydroxide / 68 h / 20 - 60 °C

4.2: 1 h / 20 °C

With 1H-tetrazole; ethanol; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane;

upstream raw materials:

fingolimod

2-amino-2-[2-(3-iodo-4-octylphenyl)ethyl]-1,3-propandiol

4-hydroxymethyl-4-[2-(3-iodo-4-octylphenyl)ethyl]oxazolidin-2-one

phosphoric acid di-tert-butyl ester 4-[2-(3-iodo-4-octylphenyl)ethyl]-2-oxooxazolidin-4-ylmethyl ester