benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate

Base Information

• Chemical Name: benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate
• CAS No.: 145696-53-3
• Molecular Formula: C₂₈H₃₆N₂O₄
• Molecular Weight: 464.605
• Mol file: 145696-53-3.mol

Synonyms:benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate

Chemical Property of benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate

There total 5 articles about benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-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: 86.0%

benzyl 5-acetoxymethyl-3-ethyl-4-methylpyrrole-2-carboxylate (56015-18-0) + tert-butyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate (75488-15-2) → benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate (145696-53-3)

Guidance literature:

With acid-activated clay; In dichloromethane; for 3h;

DOI:10.1071/CH9960265

Reference yield:

benzyl 2-methylacetoacetate (4949-45-5) → benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate (145696-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1. NaNO₂, CH₃CO₂H 2. Zn, NaOAc, CH₃CO₂H / 1.) 5 deg C, 18h 2.) 65 deg C, 1h

2: 95 percent / 33percent aq.HBr / acetic acid / 4 h / Ambient temperature

3: 56 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / Ambient temperature

4: 65 percent / Pb(OAc)4 / acetic acid / 4 h

5: 73.3 percent / TsOH / CH₂Cl₂ / 4 h / 40 °C

With lead(IV) acetate; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen bromide; sodium acetate; toluene-4-sulfonic acid; acetic acid; zinc; sodium nitrite; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)86682-5

Reference yield:

2-benzyloxycarbonyl-3-ethyl-5-methyl-pyrrole-4-carboxylic acid (128773-39-7) → benzyl-5-t-butoxycarbonyl-3',4-dimethyl-3,4'-diethyl-dipyrrylmethane-5'-carboxylate (145696-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / Ambient temperature

2: 65 percent / Pb(OAc)4 / acetic acid / 4 h

3: 73.3 percent / TsOH / CH₂Cl₂ / 4 h / 40 °C

With lead(IV) acetate; sodium tetrahydroborate; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)86682-5

upstream raw materials:

benzyl 5-acetoxymethyl-3-ethyl-4-methylpyrrole-2-carboxylate

tert-butyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate

benzyl 2-methylacetoacetate

2-benzyloxycarbonyl-3-ethyl-5-methyl-pyrrole-4-carboxylic acid

Downstream raw materials:

deoxophylloerythroetioporphyrin