(2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride

Base Information

• Chemical Name: (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride
• CAS No.: 195733-43-8
• Molecular Formula: C₂₉H₃₈N₂O₆*ClH
• Molecular Weight: 547.091
• Mol file: 195733-43-8.mol

Synonyms:3-Pyrrolidinecarboxylicacid,4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)-,monohydrochloride, (2R,3R,4S)- (9CI);3-Pyrrolidinecarboxylic acid,4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)-,monohydrochloride, [2R-(2a,3b,4a)]-;A 147627.1;Abbott 147627;Atrasentanhydrochloride;

Chemical Property of (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride

Chemical Property:

• Boiling Point: 659.4°Cat760mmHg
• Flash Point: 352.6°C
• PSA: 88.54000
• Density: 1.238g/cm³
• LogP: 5.43390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

AtrasentanHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Atrasentan, a selective antagonist of the endothelin-A (ETA) receptor, binds selectively to the ETA receptor, which may result in inhibition of endothelin-induced angiogenesis and tumor cell proliferation.

Technology Process of (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride

There total 14 articles about (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride 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:

5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3,22568-48-5) + N,N-dibutylbromoacetamide (40124-27-4) + ethyl 4-methoxybenzoylacetate (2881-83-6) → Atrasentan hydrochloride (195733-43-8)

Guidance literature:

With hydrogenchloride; sodium hydroxide; (S)-Mandelic acid; sodium ethanolate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; nickel; In tetrahydrofuran; ethanol; water; acetonitrile; at 5 - 105 ℃; for 20h;

Reference yield:

ethyl trans,trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate (173864-47-6) + N,N-dibutylbromoacetamide (40124-27-4) + (S)-Mandelic acid (17199-29-0) → Atrasentan hydrochloride (195733-43-8)

Guidance literature:

ethyl trans,trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate; (S)-Mandelic acid; In acetonitrile; at 5 - 10 ℃; Heating / reflux;

With potassium carbonate; In tetrahydrofuran; water; acetonitrile; at 25 ℃; for 1h;

N,N-dibutylbromoacetamide; With hydrogenchloride; sodium hydroxide; sodium hydrogencarbonate; more than 3 stages;

Reference yield:

atrasentan (173937-91-2) → Atrasentan hydrochloride (195733-43-8)

Guidance literature:

With hydrogenchloride; In ethanol; water; ethyl acetate; for 0.25h;

upstream raw materials:

N,N-dibutylacetamide

1,3-benzodioxole-5-acetic acid

(S)-2-Benzo[1,3]dioxol-5-yl-succinic acid 4-tert-butyl ester

2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride