(S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide

Base Information

• Chemical Name: (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide
• CAS No.: 1414642-93-5
• Molecular Formula: C₂₂H₁₇Cl₂F₆N₃O₃S
• Molecular Weight: 588.358
• Mol file: 1414642-93-5.mol

Synonyms:(S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide

Chemical Property of (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide

Chemical Property:

Purity/Quality:

>98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide

There total 13 articles about (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-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: 93.0%

3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide (1414642-56-0) → (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide (1414642-93-5)

Guidance literature:

With Chiralcel AD-H column; In ethanol; carbon dioxide; Purification / work up; Resolution of racemate;

Reference yield:

cyclopentanone (120-92-3) → (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide (1414642-93-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux

2.1: triethylamine / toluene / Reflux

3.1: water; acetic acid / tetrahydrofuran / 48 h / 20 °C

4.1: tetrachloromethane; tributylphosphine / 60 °C

4.2: -10 - 0 °C

5.1: manganese(IV) oxide / dichloromethane / 2 h / Reflux

6.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

6.2: 2 h / 20 °C / Inert atmosphere

7.1: thionyl chloride; pyridine / dichloromethane / 3 h / 20 °C

8.1: hydroxylamine hydrochloride; sodium hydroxide / water; tetrahydrofuran / 20 °C

9.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 0.5 h / 50 °C

9.2: pH 1

10.1: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 1 h / 20 °C

11.1: Chiralcel AD-H column / ethanol; carbon dioxide / Resolution of racemate

With pyridine; tetrachloromethane; manganese(IV) oxide; thionyl chloride; lithium hydroxide monohydrate; tributylphosphine; hydroxylamine hydrochloride; water; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; carbon dioxide; water; toluene; acetonitrile;

Reference yield:

1-pyrrolidinocyclopent-1-ene (7148-07-4) → (S)-3-[5-(3,5-dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid [(2,2-difluoro-ethylcarbamoyl)-methyl]-amide (1414642-93-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / toluene / Reflux

2.1: water; acetic acid / tetrahydrofuran / 48 h / 20 °C

3.1: tetrachloromethane; tributylphosphine / 60 °C

3.2: -10 - 0 °C

4.1: manganese(IV) oxide / dichloromethane / 2 h / Reflux

5.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

6.1: thionyl chloride; pyridine / dichloromethane / 3 h / 20 °C

7.1: hydroxylamine hydrochloride; sodium hydroxide / water; tetrahydrofuran / 20 °C

8.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 0.5 h / 50 °C

8.2: pH 1

9.1: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 1 h / 20 °C

10.1: Chiralcel AD-H column / ethanol; carbon dioxide / Resolution of racemate

With pyridine; tetrachloromethane; manganese(IV) oxide; thionyl chloride; lithium hydroxide monohydrate; tributylphosphine; hydroxylamine hydrochloride; water; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; carbon dioxide; water; toluene; acetonitrile;

upstream raw materials:

cyclopentanone

1-pyrrolidinocyclopent-1-ene

cyclopentane-1,2-dione

methyl [(2-oxopropyl)sulfanyl]acetate