(1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Base Information

• Chemical Name: (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide
• CAS No.: 247171-14-8
• Molecular Formula: C₂₂H₂₁BrN₂O₃
• Molecular Weight: 441.324
• Mol file: 247171-14-8.mol

Synonyms:(1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Chemical Property of (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

There total 5 articles about (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide 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: 64.0%

carbon monoxide (201230-82-2) + 2-bromoaniline (615-36-1) + (1S,6R,9S)-formic acid 7-benzyl-4-iodo-8-oxo-7-azabicyclo[4.2.1]non-3-en-9-yl ester (247171-09-1) → (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide (247171-14-8)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 40 ℃; for 20h;

DOI:10.1021/jo001119t

Reference yield:

1-benzyl-5-ethoxy-4-hydroxy-3-(buta-2,3-dienyl)-2-pyrrolidinone (199103-44-1) → (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide (247171-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / sodium iodide / 18 h / 85 °C

2: 64 percent / Pd(OAc)2; triphenylphosphine; triethylamine / dimethylformamide / 20 h / 40 °C

With palladium diacetate; triethylamine; triphenylphosphine; sodium iodide; In N,N-dimethyl-formamide;

DOI:10.1021/jo001119t

Reference yield:

Formic acid (1S,6R,9S)-7-benzyl-4-(2-bromo-phenylcarbamoyl)-8-oxo-7-aza-bicyclo[4.2.1]non-3-en-9-yl ester → (1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide (247171-14-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 0.25h;

DOI:10.1002/(SICI)1521-3773(19990802)38:15<2214::AID-ANIE2214>3.0.CO;2-V

upstream raw materials:

carbon monoxide

2-bromoaniline

(1S,6R,9S)-formic acid 7-benzyl-4-iodo-8-oxo-7-azabicyclo[4.2.1]non-3-en-9-yl ester

1-benzyl-5-ethoxy-4-hydroxy-3-(buta-2,3-dienyl)-2-pyrrolidinone

Downstream raw materials:

C₂₃H₂₂N₂O₃

C₂₄H₂₄N₂O₃

(1S,6R)-7-benzyl-9-methylene-8-oxo-7-azabicyclo[4.2.1]non-3-ene-4-carboxylic acid benzyl-(2-bromophenyl)amide

C₃₀H₂₆N₂O₂