dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]

Base Information

• Chemical Name: dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]
• CAS No.: 341554-40-3
• Molecular Formula: C₁₈H₂₁NO₈
• Molecular Weight: 379.367
• Mol file: 341554-40-3.mol

Synonyms:dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]

Chemical Property of dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate]

There total 3 articles about dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] 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: 86.0%

dimethyl {N-[(2R,3S)-3-acetoxy-2-bromobutyryl]-N-(4-methoxyphenyl)aminomalonate} (341554-39-0) → dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] (341554-40-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 20 ℃;

DOI:10.1016/S0957-4166(01)00003-9

Reference yield:

(2R,3S)-3-acetoxy-2-bromobutyryl chloride (161906-03-2) → dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] (341554-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / toluene / 48 h / 80 °C

2: 86 percent / DBU / benzene / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; benzene;

DOI:10.1016/S0957-4166(01)00003-9

Reference yield:

(2R,3S)-3-Acetoxy-2-bromo-butyric acid (341554-38-9) → dimethyl [(αS,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2,2-dicarboxylate] (341554-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / SOCl₂ / CH₂Cl₂ / 8 h / 60 °C

2: 88 percent / toluene / 48 h / 80 °C

3: 86 percent / DBU / benzene / 20 °C

With thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; benzene;

DOI:10.1016/S0957-4166(01)00003-9

upstream raw materials:

dimethyl {N-[(2R,3S)-3-acetoxy-2-bromobutyryl]-N-(4-methoxyphenyl)aminomalonate}

(2R,3S)-3-acetoxy-2-bromobutyryl chloride

(2R,3S)-3-Acetoxy-2-bromo-butyric acid

Downstream raw materials:

(αS,3S)-3-(1-acetoxyethyl)-2-methoxycarbonyl-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylic acid

methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate]

methyl [(αS,2SR,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate]

(αS,3S,4S)-3-(1-acetoxyethyl)-4-hydroxymethyl-N-(4-methoxyphenyl)-azetidin-2-one