(Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester
• CAS No.: 104430-41-3
• Molecular Formula: C₁₅H₁₆N₂O₄S
• Molecular Weight: 320.369
• Mol file: 104430-41-3.mol

Synonyms:(Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester

Chemical Property of (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester

There total 1 articles about (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic 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: 35.0%

(1S,5R)-3-benzyl-6-(2-bromo-1-hydroxy-2-methylpropyl)-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one (74213-36-8,74243-81-5,104486-77-3) + cis-β-(methoxycarbonyl)vinylisothiouronium chloride (69077-84-5) → (Z)-3-((2S,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester (104486-78-4) + (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester (104430-41-3)

Guidance literature:

With triethylamine; Yield given. Multistep reaction; 1.) dichloromethane;

DOI:10.1016/S0040-4039(00)84243-4

Reference yield: 84.0%

tert-butyl glyoxylate (7633-32-1) + (Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester (104430-41-3) → (Z)-3-[(2R,3R)-1-(tert-Butoxycarbonyl-hydroxy-methyl)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl]-acrylic acid methyl ester (104430-42-4,104486-79-5)

Guidance literature:

In tetrahydrofuran; triethylamine;

DOI:10.1016/S0040-4039(00)84243-4

Reference yield:

(Z)-3-((2R,3R)-4-Oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl)-acrylic acid methyl ester (104430-41-3) → (4R,6R,7R)-4-Methoxycarbonylmethyl-8-oxo-7-phenylacetylamino-3,5-dithia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid (104430-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / tetrahydrofuran; triethylamine

2: 1.) thionyl chloride/2,6-lutidine 2.) hydrogen sulphide/triethylamine

3: 96 percent / trifluoroacetic acid

With 2,6-dimethylpyridine; thionyl chloride; hydrogen sulfide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; triethylamine;

DOI:10.1016/S0040-4039(00)84243-4

upstream raw materials:

(1S,5R)-3-benzyl-6-(2-bromo-1-hydroxy-2-methylpropyl)-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one

cis-β-(methoxycarbonyl)vinylisothiouronium chloride

Downstream raw materials:

(Z)-3-[(2R,3R)-1-(tert-Butoxycarbonyl-hydroxy-methyl)-4-oxo-3-phenylacetylamino-azetidin-2-ylsulfanyl]-acrylic acid methyl ester

(4R,6R,7R)-4-Methoxycarbonylmethyl-8-oxo-7-phenylacetylamino-3,5-dithia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid

(4R,6R,7R)-4-Methoxycarbonylmethyl-8-oxo-7-phenylacetylamino-3,5-dithia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid tert-butyl ester