2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

Base Information

• Chemical Name: 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione
• CAS No.: 115936-46-4
• Molecular Formula: C₂₃H₂₂N₂O₆
• Molecular Weight: 422.437
• Mol file: 115936-46-4.mol

Synonyms:2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

Chemical Property of 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

There total 5 articles about 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-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%

N-ethoxycarbonylphthalimide (22509-74-6) + (3R,4R)-cis-1-(p-anisyl)-3-amino-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-85-8) → 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione (115936-46-4)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1021/jo00253a013

Reference yield:

N-phthaloylglycine chloride (6780-38-7) + [1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-24-0) → 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione (115936-46-4)

Guidance literature:

With triethylamine; In dichloromethane; at -20 - 20 ℃;

DOI:10.1016/S0040-4020(99)00867-4

Reference yield:

(3R,4R)-cis-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (103173-99-5) → 2-((2R,3R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione (115936-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂S gas; Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 70 percent / sodium carbonate / tetrahydrofuran / 0.75 h / 20 °C

With hydrogen sulfide; sodium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Substitution;

DOI:10.1016/S0040-4020(00)00410-5

upstream raw materials:

N-phthaloylglycine chloride

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

N-ethoxycarbonylphthalimide

(3R,4R)-cis-1-(p-anisyl)-3-amino-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Downstream raw materials:

(3R,4R)-cis-1-(p-anisyl)-3-amino-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(3S,4R)-trans-1-(p-anisyl)-3-phthalimido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

(-)-cis-4-(R)-[1(S),2-dihydroxyethyl]-1-(4-methoxyphenyl)-3-(R)-phthalimidyl-azetidin-2-one

(+)-cis-3-(R)-phthalimidyl-4-(R)-formyl-1-(4-methoxyphenyl)-azetidin-2-one