2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid

Base Information

• Chemical Name: 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid
• CAS No.: 74516-47-5
• Molecular Formula: C₇H₈O₃S*C₁₅H₁₇ClN₂O₃
• Molecular Weight: 480.969
• Mol file: 74516-47-5.mol

Synonyms:2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid

Chemical Property of 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid

There total 2 articles about 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic 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: 65.0%

1,2-secopenicillin tosylate (74280-93-6) → 2-((2R,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid (74560-12-6) + 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid (74516-47-5)

Guidance literature:

With chlorine; In tetrachloromethane; dichloromethane; at -65 ℃; for 1h;

DOI:10.1021/jm00184a009

Reference yield:

→ 1,2-secopenicillin tosylate (74280-93-6) + 2-((2S,3R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid (74516-47-5)

Guidance literature:

With methanol; chlorine; In tetrachloromethane; dichloromethane; at -65 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jm00184a009

Reference yield:

ethylene glycol (107-21-1) + 2-((R)-3-Amino-2-chloro-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid benzyl ester; compound with toluene-4-sulfonic acid (72217-18-6,72217-20-0,74516-47-5,74560-12-6) → 2-[(S)-3-Amino-2-(2-hydroxy-ethoxy)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester (72217-21-1,72217-22-2)

Guidance literature:

With silver tetrafluoroborate; In dichloromethane; at -45 - 0 ℃; for 2.08333h;

DOI:10.1021/jm00184a009

upstream raw materials:

1,2-secopenicillin tosylate

Downstream raw materials:

2-[(S)-3-Amino-2-(2-hydroxy-ethoxy)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester

benzyl 2-[2-oxo-3β-phenoxyacetamido-4β-(2-phenoxyacetoxyethoxy)azetidin-1-yl]glyoxylate

benzyl 2-chloro-2-[2-oxo-3β-phenoxyacetamido-4β-(2-phenoxyacetoxyethoxy)azetidin-1-yl]acetate

benzyl 2-[2-oxo-3β-phenoxyacetamido-4β-(2-phenoxyacetoxyethoxy)azetidin-1-yl]glycolate