(5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione

Base Information

• Chemical Name: (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione
• CAS No.: 331258-63-0
• Molecular Formula: C₂₅H₂₅NO₄
• Molecular Weight: 403.478

Synonyms:(5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione

Chemical Property of (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione

Chemical Property:

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Technology Process of (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione

There total 3 articles about (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione 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: 70.0%

(5R,6R,7S,8R)-5-Acetyl-6-hydroxy-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-en-9-one (251480-09-8) → (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione (331258-63-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo005715z

Reference yield:

(+)-(3R,4R)-cis-4-formyl-3-phenoxy-1-(2-propynyl)-2-azetidinone (251480-02-1) → (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione (331258-63-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / DABCO / acetonitrile / 72 h / -20 °C

2: 60 percent / 3 h / 210 °C

3: 70 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; acetonitrile; 1: Baylis-Hillman reaction / 3: Swern oxidation;

DOI:10.1021/jo005715z

Reference yield:

(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-3-phenoxy-1-(2-propynyl)-2-azetidinone (251480-05-4) → (5S,7R,8R)-5-Acetyl-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-ene-6,9-dione (331258-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / 3 h / 210 °C

2: 70 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 2: Swern oxidation;

DOI:10.1021/jo005715z

upstream raw materials:

(5R,6R,7S,8R)-5-Acetyl-6-hydroxy-8-phenoxy-5-(2-p-tolyl-ethyl)-1-aza-bicyclo[5.2.0]non-3-en-9-one

(+)-(3R,4R)-cis-4-formyl-3-phenoxy-1-(2-propynyl)-2-azetidinone

(3R,4S)-4-[(R)-1-hydroxy-2-methylidene-3-oxobutyl]-3-phenoxy-1-(2-propynyl)-2-azetidinone

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