methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Base Information

• Chemical Name: methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate
• CAS No.: 80559-16-6
• Molecular Formula: C₁₉H₂₁ClN₂O₈
• Molecular Weight: 440.837
• Mol file: 80559-16-6.mol

Synonyms:methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Chemical Property of methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

There total 8 articles about methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate 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: 84.0%

methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate (80559-15-5) → methyl 2-[(3S)-4-chloro-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (80527-82-8,80559-16-6,80559-17-7,80559-18-8,102919-74-4)

Guidance literature:

With chlorine; In tetrachloromethane; dichloromethane; at -78 - 0 ℃; cis/trans ratio: 45:55;

DOI:10.1016/S0040-4039(00)87743-6

Reference yield: 46.0%

methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-but-2-enoate (76855-55-5) → methyl 2-[(3S,4R)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (80527-82-8) + methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (80559-16-6)

Guidance literature:

With chlorine; In tetrachloromethane; dichloromethane; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(00)87743-6

Reference yield:

(3S,4R)-3-(1-hidroxyethyl)-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-methylthio-2-azetidinone (74614-77-0,76899-00-8,76899-01-9) → methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (80559-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-Dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 0 °C

2: 46 percent / Cl₂ / CH₂Cl₂; CCl₄ / -78 - 0 °C

With dmap; chlorine; In tetrachloromethane; dichloromethane;

DOI:10.1016/S0040-4039(00)87743-6

upstream raw materials:

methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate

(3S,4R)-3-(1-hidroxyethyl)-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-methylthio-2-azetidinone

4-nitrobenzyl chloroformate

methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-but-2-enoate

Downstream raw materials:

methyl 2-[(3S,4R)-4-{2-(methoxycarbonylmethyl)allyl}-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

p-nitrobenzyl 4-[(2R,3S)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

(3S,4R)-3-[(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)-2-oxoazetidine

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine