(R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester

Base Information

• Chemical Name: (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester
• CAS No.: 83242-27-7
• Molecular Formula: C₃₀H₂₆ClN₃O₄S₃
• Molecular Weight: 624.205
• Mol file: 83242-27-7.mol

Synonyms:(R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester

Chemical Property of (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester

There total 4 articles about (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl 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: 81.0%

2-benzothiazolylsulfenyl chloride (33405-92-4) + (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester (83290-69-1) → (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester (83242-27-7)

Guidance literature:

In 1,4-dioxane; water; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87378-5

Reference yield:

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester (86832-59-9) → (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester (83242-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 percent / NaCl, H₂SO₄ / H₂O; CHCl₃ / Ambient temperature; electrolysis with Pt electrodes at a constant current (10 mA/cm²), lower Cl(-) concentration

2: 81 percent / aqueous HCl

With hydrogenchloride; sulfuric acid; sodium chloride; In chloroform; water;

DOI:10.1002/bscb.19820911202

Reference yield:

(R)-3-Chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester (86832-60-2) → (R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-chloromethyl-but-3-enoic acid benzyl ester (83242-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc dust, AcOH / CH₂Cl₂ / 0 - 2 °C

2: 81 percent / aqueous HCl

With hydrogenchloride; acetic acid; zinc; In dichloromethane;

DOI:10.1002/bscb.19820911202

upstream raw materials:

2-benzothiazolylsulfenyl chloride

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-but-3-enoic acid benzyl ester

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester

(R)-3-Chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester

Downstream raw materials:

(6R,7R)-3-(Benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester