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

Base Information

• Chemical Name: tert-Butyl (4Z)-1-benzyloxycarbonylmethylene-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1,2,3,10-tetrahydrodipyrrin-9-carboxylate
• CAS No.: 145046-06-6
• Molecular Formula: C₃₂H₄₀N₂O₈
• Molecular Weight: 580.678
• Mol file: 145046-06-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about tert-Butyl (4Z)-1-benzyloxycarbonylmethylene-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1,2,3,10-tetrahydrodipyrrin-9-carboxylate 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: 35.0%

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 2-trimethylsilanyl-ethyl ester (145045-89-2,145046-05-5) → tert-Butyl (4Z)-1-benzyloxycarbonylmethylene-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1,2,3,10-tetrahydrodipyrrin-9-carboxylate (145045-91-6,145046-06-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 17h;

DOI:10.1039/P19920002175

Reference yield:

Benzyl tert-butyl bromomalonate (78815-40-4) → 5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (145046-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diazabicyclo-undecane / toluene / 1 h / 18 °C

2: triphenylphosphine / toluene / 1.25 h / Heating

3: trifluoroacetic acid / 3 h / 18 °C

With diazabicyclo-undecane; triphenylphosphine; trifluoroacetic acid; In toluene;

Reference yield:

t-butyl 1,2,3,10-tetrahydro-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1-thioxodipyrrin-9-carboxylate (145045-86-9) → 5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (145046-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diazabicyclo-undecane / toluene / 1 h / 18 °C

2: triphenylphosphine / toluene / 1.25 h / Heating

3: trifluoroacetic acid / 3 h / 18 °C

With diazabicyclo-undecane; triphenylphosphine; trifluoroacetic acid; In toluene;

upstream raw materials:

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

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

Benzyl tert-butyl bromomalonate

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

Downstream raw materials:

C₄₆H₅₄N₄O₁₁

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

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