Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester

Base Information

• Chemical Name: Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester
• CAS No.: 76227-74-2
• Molecular Formula: C₁₅H₁₄N₄O₅S
• Molecular Weight: 362.366
• Mol file: 76227-74-2.mol

Synonyms:Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester

Chemical Property of Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester

There total 2 articles about Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester 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: 97.0%

methyl diazomalonyl chloride (60180-61-2) + 2-oxo-3β-(2-phenylacetamido)-4β-mercaptoazetidine (74643-21-3) → Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester (76227-74-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)77414-4

Reference yield:

(1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one (34103-69-0) → Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester (76227-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1N HCl / methanol / 0.5 h / 20 °C

2: 97 percent / Et₃N / CH₂Cl₂ / 0 °C

With hydrogenchloride; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)77414-4

Reference yield:

Diazo-((2R,3R)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester (76227-74-2) → ((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester (76227-76-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)77414-4

upstream raw materials:

methyl diazomalonyl chloride

2-oxo-3β-(2-phenylacetamido)-4β-mercaptoazetidine

(1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

Downstream raw materials:

2-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-malonic acid dimethyl ester

((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanylcarbonyl)-acetic acid methyl ester