Etrasimod

Base Information

• Chemical Name: Etrasimod
• CAS No.: 1206123-37-6
• Molecular Formula: C26H26F3NO3
• Molecular Weight: 457.493
• Mol file: 1206123-37-6.mol

Synonyms:Etrasimod;APD334;Neflamapimod;(R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

Chemical Property of Etrasimod

Chemical Property:

• Boiling Point: 621.4±50.0 °C(Predicted)
• PKA: 4.61±0.10(Predicted)
• PSA: 62.32000
• Density: 1.326±0.06 g/cm3(Predicted)
• LogP: 6.92780

Purity/Quality:

98% ^*data from raw suppliers

Etrasimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Etrasimod

There total 25 articles about Etrasimod 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:

(R/S)-ethyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (1206124-34-6) → [(3R)-7-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (1206123-37-6)

Guidance literature:

(R/S)-ethyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate; With water; recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150; In acetonitrile; at 40 ℃; for 16h; pH=7.8; Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer;

With citric acid; In water; acetonitrile; pH=3.96; Product distribution / selectivity;

Reference yield:

2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid (1206123-55-8) → (S)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid (1206123-51-4) + [(3R)-7-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (1206123-37-6)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; Resolution of racemate;

Reference yield:

o-trifluoromethylphenyl bromide (392-83-6) → [(3R)-7-{[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (1206123-37-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N,N,N,-tetramethylethylenediamine; magnesium / iron(III) chloride / tetrahydrofuran / 20 - 30 °C / Inert atmosphere

2.1: thionyl chloride; sulfuric acid / -5 - 20 °C / Inert atmosphere

3.1: caesium carbonate / acetonitrile / 40 - 65 °C / Inert atmosphere

4.1: water / recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150 / acetonitrile / 16 h / 40 °C / pH 7.8 / Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer

4.2: pH 3.96

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; water; caesium carbonate; magnesium; iron(III) chloride; In tetrahydrofuran; acetonitrile;

upstream raw materials:

2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

cyclopentanone

4-chloro-3-trifluoromethylbenzoic acid methyl ester

2-ethoxycarbonyl-1-cyclopentanone

Refernces

• 1、 -. "COMPOUNDS USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS". . . Retrieved 2020/03/29.
• 2、 -. "PROCESSES FOR THE PREPARATION OF (R)-2-(7-(4-CYCLOPENTYL-3-(TRIFLUOROMETHYL)BENZYLOXY)-1,2,3,4-TETRAHYDROCYCLOPENTA[B]INDOL-3-YL)ACETIC ACID AND SALTS THEREOF". . . Retrieved 2011/08/21.