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

Base Information

Chemical Name:(1S,6R)-7-benzyl-8,9-dioxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide
CAS No.:247171-15-9
Molecular Formula:C₂₂H₁₉BrN₂O₃
Molecular Weight:439.308
Hs Code.:

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

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

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

There total 6 articles about (1S,6R)-7-benzyl-8,9-dioxo-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: 66.0%

: 247171-14-8
(1S,6R,9S)-7-benzyl-9-hydroxy-8-oxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

: 247171-15-9
(1S,6R)-7-benzyl-8,9-dioxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 40 ℃; for 24h;
DOI:10.1002/(SICI)1521-3773(19990802)38:15<2214::AID-ANIE2214>3.0.CO;2-V

Reference yield:

: 199103-44-1
1-benzyl-5-ethoxy-4-hydroxy-3-(buta-2,3-dienyl)-2-pyrrolidinone

: 247171-15-9
(1S,6R)-7-benzyl-8,9-dioxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 66 percent / PCC / CH₂Cl₂ / 17 h / 40 °C

With palladium diacetate; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo001119t

Reference yield:

: 247171-09-1
(1S,6R,9S)-formic acid 7-benzyl-4-iodo-8-oxo-7-azabicyclo[4.2.1]non-3-en-9-yl ester

: 247171-15-9
(1S,6R)-7-benzyl-8,9-dioxo-7-azabicyclo[4.2.1]non-3-en-4-carboxylic acid (2-bromophenyl)amide

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / Pd(OAc)2; triphenylphosphine; triethylamine / dimethylformamide / 20 h / 40 °C

2: 66 percent / PCC / CH₂Cl₂ / 17 h / 40 °C

With palladium diacetate; triethylamine; triphenylphosphine; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo001119t