3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester

Base Information

• Chemical Name: 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester
• CAS No.: 316129-35-8
• Molecular Formula: C₂₃H₂₅ClN₂O₃Se
• Molecular Weight: 491.876

Synonyms:3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester

Chemical Property of 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester

There total 9 articles about 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl 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: 96.0%

tert-butyl 5-formyl-3-<2-(methyoxycarbonyl)ethyl>-4-methylpyrrole-2-carboxylate (53751-01-2) + 2-(tert-butyldimethylsilanyloxy)-3-[2-(4-chlorophenylselanyl)ethyl]-4-methylpyrrole-1-carboxylic acid, tert-butyl ester (316129-33-6) → 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester (316129-35-8)

Guidance literature:

tert-butyl 5-formyl-3-<2-(methyoxycarbonyl)ethyl>-4-methylpyrrole-2-carboxylate; 2-(tert-butyldimethylsilanyloxy)-3-[2-(4-chlorophenylselanyl)ethyl]-4-methylpyrrole-1-carboxylic acid, tert-butyl ester; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.166667h;

With trifluoroacetic acid; at 23 ℃; for 8h; Further stages.;

DOI:10.1021/jo005531k

Reference yield:

bis(p-chlorophenyl) diselenide (20541-49-5) → 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester (316129-35-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaBH₄ / ethanol / 0.5 h / 0 °C

2.1: 12.43 g / ethanol; tetrahydrofuran / Heating

3.1: 100 percent / (COCl)2 / CH₂Cl₂ / 4 h / 20 °C

4.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

5.1: 10.17 g / aq. HCl / CH₂Cl₂ / 1 h

6.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 60 percent / t-BuOK / tetrahydrofuran / 0.33 h / -10 °C

8.1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

9.1: TiCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

9.2: 96 percent / TFA / 8 h / 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; oxalyl dichloride; potassium tert-butylate; titanium tetrachloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo005531k

Reference yield:

sodium p-chlorophenylselenide (41491-33-2) → 3-(5-{4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl}-4-methyl-1H-pyrrol-3-yl)-propionic acid methyl ester (316129-35-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 12.43 g / ethanol; tetrahydrofuran / Heating

2.1: 100 percent / (COCl)2 / CH₂Cl₂ / 4 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

4.1: 10.17 g / aq. HCl / CH₂Cl₂ / 1 h

5.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

6.1: 60 percent / t-BuOK / tetrahydrofuran / 0.33 h / -10 °C

7.1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

8.1: TiCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

8.2: 96 percent / TFA / 8 h / 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; oxalyl dichloride; potassium tert-butylate; titanium tetrachloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo005531k

upstream raw materials:

tert-butyl 5-formyl-3-<2-(methyoxycarbonyl)ethyl>-4-methylpyrrole-2-carboxylate

2-(tert-butyldimethylsilanyloxy)-3-[2-(4-chlorophenylselanyl)ethyl]-4-methylpyrrole-1-carboxylic acid, tert-butyl ester

bis(p-chlorophenyl) diselenide

sodium p-chlorophenylselenide

Downstream raw materials:

3-[5-[4-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-5-oxo-1,5-dihydropyrrol-2-ylidenemethyl]-2-formyl-4-methyl-1H-pyrrol-3-yl]propionic acid, methyl ester

C₄₁H₄₅ClN₄O₆Se

C₄₁H₄₅ClN₄O₆Se

C₄₀⁽¹³⁾CH₄₅ClN₄O₆Se

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