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

Base Information

• Chemical Name: methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate]
• CAS No.: 341554-43-6
• Molecular Formula: C₁₆H₁₉NO₆
• Molecular Weight: 321.33
• Mol file: 341554-43-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] 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: 65.0%

methyl [(αS,2SR,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] (341554-42-5) → (αS,3S,4S)-3-(1-acetoxyethyl)-4-hydroxymethyl-N-(4-methoxyphenyl)-azetidin-2-one (341554-44-7) + methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] (341554-43-6)

Guidance literature:

With sodium tetrahydroborate; In tert-butyl alcohol; at 20 ℃; for 1.33333h; Heating;

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

Reference yield:

(2R,3S)-3-acetoxy-2-bromobutyryl chloride (161906-03-2) → methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] (341554-43-6)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 86 percent / DBU / benzene / 20 °C

3: 58 percent / aq. NaOH; pyridine / 5 °C

4: 67 percent / α-picoline / 1.33 h / Heating

5: 65 percent / NaBH₄ / 2-methyl-propan-2-ol / 1.33 h / 20 °C / Heating

With pyridine; α-picoline; sodium hydroxide; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; tert-butyl alcohol; benzene;

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

Reference yield:

(2R,3S)-3-Acetoxy-2-bromo-butyric acid (341554-38-9) → methyl [(αS,2R,3S)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] (341554-43-6)

Guidance literature:

Multi-step reaction with 6 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

4: 58 percent / aq. NaOH; pyridine / 5 °C

5: 67 percent / α-picoline / 1.33 h / Heating

6: 65 percent / NaBH₄ / 2-methyl-propan-2-ol / 1.33 h / 20 °C / Heating

With pyridine; α-picoline; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; tert-butyl alcohol; benzene;

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

upstream raw materials:

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

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

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

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