(1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione

Base Information

• Chemical Name: (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione
• CAS No.: 131065-64-0
• Molecular Formula: C₁₄H₁₂FN₃O₄
• Molecular Weight: 305.265

Synonyms:(1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione

Chemical Property of (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione

Chemical Property:

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Technology Process of (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione

There total 2 articles about (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-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: 73.0%

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + cis-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene (131101-27-4) → (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (131065-64-0)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

Reference yield:

fluorobenzene (462-06-6) → (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (131065-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene dioxygenase from intact cells of Pseudomonas putida UV₄, O₂

2: 73 percent / CH₂Cl₂ / 1 h / Ambient temperature

With toluene dioxygenase from intact cells of Pseudomonas putida UV₄; oxygen; In dichloromethane;

Reference yield: 100.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione (131065-64-0) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.02,6]undec-10-en-8-yl ester (131043-58-8)

Guidance literature:

With pyridine;

DOI:10.1021/ja00002a040

upstream raw materials:

4-Phenyl-1,2,4-triazolidine-3,5-dione

cis-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene

fluorobenzene

Downstream raw materials:

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-3,5-dioxo-4-phenyl-9-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester

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