[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid

Base Information

• Chemical Name: [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid
• CAS No.: 1001387-56-9
• Molecular Formula: C₂₄H₂₄ClNO₆
• Molecular Weight: 457.911
• Mol file: 1001387-56-9.mol

Synonyms:[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid

Chemical Property of [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid

There total 14 articles about [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid 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: 14.0%

[8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid → [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-56-9) + [(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-55-8) + C24H24ClNO6

Guidance literature:

Resolution of racemate;

DOI:10.1016/j.bmcl.2011.04.092

Reference yield:

[8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid → [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-56-9) + [(4S,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-53-6) + [(4R,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-54-7) + [(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-55-8)

Guidance literature:

With Daicel Chiralpak AD-H; In 2-Methylpentane; water; acetic acid; isopropyl alcohol; at 25 ℃; Resolution of racemate;

Reference yield:

2-(3-methyl-1-butyn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → [(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-56-9) + [(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-isopropyl-4H,6H-[2]benzoxepino[4,5-c]isoxazol-4-yl]acetic acid (1001387-55-8) + C24H24ClNO6

Guidance literature:

Multi-step reaction with 8 steps

1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 56 h / 50 °C

2: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dichloromethane / 72 h / 85 °C

3: hydrogenchloride / tetrahydrofuran; water / 42 h / Reflux

4: dichloromethane / 16 h / 20 °C

5: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / 0 °C

6: 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ⁵,4Λ⁵-catenadi(phosphazene) / tetrahydrofuran / 1 h / 0 °C

7: hydrogenchloride / 1,4-dioxane; water / 19 h / 80 °C

8: Resolution of racemate

With hydrogenchloride; potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium hydrogencarbonate; 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ⁵,4Λ⁵-catenadi(phosphazene); lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; 2: Suzuki coupling / 4: Wittig olefination;

DOI:10.1016/j.bmcl.2011.04.092

upstream raw materials:

3-(Dimethoxymethyl)-5-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

(5-Chloro-2-iodophenyl)(2,3-dimethoxyphenyl)methanone

{5-Chloro-2-[3-(dimethoxymethyl)-5-isopropylisoxazol-4-yl]phenyl}(2,3-dimethoxyphenyl)-methanone

C₂₆H₂₆ClNO₆