1H-Pyrrole-2,5-dicarboxylic acid, 3-(2-methoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-, 2-(1,1-dimethylethyl) 5-(phenylmethyl) ester

Base Information

• Chemical Name: 1H-Pyrrole-2,5-dicarboxylic acid, 3-(2-methoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-, 2-(1,1-dimethylethyl) 5-(phenylmethyl) ester
• CAS No.: 84315-30-0
• Molecular Formula: C₂₄H₂₉NO₈
• Molecular Weight: 459.496
• Mol file: 84315-30-0.mol

Synonyms:

Chemical Property of 1H-Pyrrole-2,5-dicarboxylic acid, 3-(2-methoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-, 2-(1,1-dimethylethyl) 5-(phenylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrole-2,5-dicarboxylic acid, 3-(2-methoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-, 2-(1,1-dimethylethyl) 5-(phenylmethyl) ester

There total 8 articles about 1H-Pyrrole-2,5-dicarboxylic acid, 3-(2-methoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-, 2-(1,1-dimethylethyl) 5-(phenylmethyl) 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:

3-(2-Methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2,5-dicarboxylic acid dibenzyl ester → t-butyl 5-benzyloxycarbonyl-4-(2-methoxycarbonylethyl)-3-methoxycarbonylmethylpyrrole-2-carboxylat (84315-30-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C

2: thionyl chloride / 1 h / 20 °C

3: N,N-dimethylaniline / CH₂Cl₂ / 20 °C

With thionyl chloride; hydrogen; N,N-dimethyl-aniline; palladium on activated charcoal; In dichloromethane;

DOI:10.1039/P19870000287

Reference yield:

5-Chlorocarbonyl-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid benzyl ester (74855-24-6) + tert-butyl alcohol (75-65-0) → t-butyl 5-benzyloxycarbonyl-4-(2-methoxycarbonylethyl)-3-methoxycarbonylmethylpyrrole-2-carboxylat (84315-30-0)

Guidance literature:

With N,N-dimethyl-aniline; In dichloromethane; at 20 ℃; Yield given;

DOI:10.1039/P19870000287

Reference yield:

diethyl 3-oxoadipate (7149-59-9) → t-butyl 5-benzyloxycarbonyl-4-(2-methoxycarbonylethyl)-3-methoxycarbonylmethylpyrrole-2-carboxylat (84315-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 97.5 percent / 3 h / 150 - 160 °C

2: 1.) sodium nitrite, 2.) zinc dust, ammonium acetate / 1) acetic acid. 15 - 20 deg C, 1 d; 2) acetic acid, 90 - 100 deg C, 0. 5 h

3: 1.) thallium(III) nitrate trihydrate, nitric acid / 1) 30 h; 2) 1 d

4: 80.1 percent / sulphuryl chloride / CH₂Cl₂ / 2 h

5: 44.0 g / sulphuric acid / CHCl₃ / 40 h / Ambient temperature

With ammonium acetate; sulfuryl dichloride; thallium(III) nitrate trihydrate; sulfuric acid; nitric acid; zinc; sodium nitrite; In dichloromethane; chloroform;

upstream raw materials:

5-Chlorocarbonyl-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid benzyl ester

tert-butyl alcohol

Isobutane

5-benzyloxycarbonyl-4-(2-methoxycarbonylethyl)-3methoxycarbonylmethylpyrrole-2-carboxylic acid

Downstream raw materials:

tert-butyl 3,3'-bis<β-(methoxycarbonyl)ethyl>-4,4'--5'-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate

benzyl 5'-t.butyloxycarbonyl-4,3'-di(2-methoxycarbonylethyl)-3,4'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5-carboxylate

3,3'-bis-(2-methoxycarbonyl-ethyl)-4,4'-bis-methoxycarbonylmethyl-1H,1'H-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid dibenzyl ester

Refernces

• 1、 Battersby, Alan R.,Fookes, Christopher J. R.,Gustafson-Potter, Kerstin E.,McDonald, Edward,Matcham, George W. J.. "Biosynthesis of Porphyrins and Related Macrocycles. Part 17. Chemical and Enzymic Transformation of Isomeric Aminomethylbilanes into Uroporphyrinogens: Proof that Unrearranged Bilane is the Preferred Enzymic Substrate and Detection of a Transient Intermed". . p. 2413 - 2426. Retrieved 2007/10/02.