3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester

Base Information

• Chemical Name: 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester
• CAS No.: 145045-92-7
• Molecular Formula: C₂₇H₃₂N₂O₆
• Molecular Weight: 480.561
• Mol file: 145045-92-7.mol

Synonyms:

Chemical Property of 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester

There total 5 articles about 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-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: 60.0%

2-[5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-pyrrolidin-(2Z)-ylidene]-malonic acid benzyl ester tert-butyl ester (145045-90-5) → 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester (145045-92-7)

Guidance literature:

With trifluoroacetic acid; for 2.5h;

DOI:10.1039/P19920002175

Reference yield:

t-butyl 1,2,3,10-tetrahydro-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1-thioxodipyrrin-9-carboxylate (145045-86-9) → 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester (145045-92-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / DBU / CH₂Cl₂ / 1.08 h

2: 82.5 percent / DBU, Ph₃P / toluene / 1 h / Heating

3: 35 percent / Bu₄NF / tetrahydrofuran / 17 h / 50 °C

4: CF₃CO₂H / 2.5 h

With tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/P19920002175

Reference yield:

2-[5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-pyrrolidin-(2Z)-ylidene]-malonic acid benzyl ester 2-trimethylsilanyl-ethyl ester (145045-89-2,145046-05-5) → 3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester (145045-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / Bu₄NF / tetrahydrofuran / 17 h / 50 °C

2: CF₃CO₂H / 2.5 h

With tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1039/P19920002175

upstream raw materials:

tert-Butyl (4Z)-1-benzyloxycarbonylmethylene-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1,2,3,10-tetrahydrodipyrrin-9-carboxylate

2-[5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-pyrrolidin-(2Z)-ylidene]-malonic acid benzyl ester tert-butyl ester

t-butyl 1,2,3,10-tetrahydro-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1-thioxodipyrrin-9-carboxylate

2-[5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-pyrrolidin-(2Z)-ylidene]-malonic acid benzyl ester 2-trimethylsilanyl-ethyl ester

Downstream raw materials:

Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate

C₄₆H₅₄N₄O₁₁