5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-(bromomethylene)-8-oxo-, diphenylmethyl ester, (6R,7E)-

Base Information

Chemical Name:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-(bromomethylene)-8-oxo-, diphenylmethyl ester, (6R,7E)-
CAS No.:162253-01-2
Molecular Formula:C24H20BrNO5S
Molecular Weight:514.397
Hs Code.:
Mol file:162253-01-2.mol

Synonyms:

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Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-(bromomethylene)-8-oxo-, diphenylmethyl ester, (6R,7E)-

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-(bromomethylene)-8-oxo-, diphenylmethyl ester, (6R,7E)-

There total 9 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-(bromomethylene)-8-oxo-, diphenylmethyl ester, (6R,7E)- 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: 85.0%

: 162252-93-9
benzhydryl 7-(dibromomethylene)cephalosporanate

: 162253-01-2
(R)-3-Acetoxymethyl-7-[1-bromo-meth-(E)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: With ammonium chloride; zinc; In methanol;
DOI:10.1016/S0040-4039(98)02691-4

Reference yield:

: 59128-53-9
benzhydryl 7-oxocephalosporanate

: 162253-01-2
(R)-3-Acetoxymethyl-7-[1-bromo-meth-(E)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 2 steps

1: PPh₃ / CH₂Cl₂ / 0 °C

2: NH₄Cl; Zn / methanol; tetrahydrofuran / 0 - 20 °C

With ammonium chloride; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane; 1: Substitution / 2: Reduction;
DOI:10.1016/S0040-4020(00)00426-9

Reference yield:

: 908093-98-1
diazodiphenylmethane

: 162253-01-2
(R)-3-Acetoxymethyl-7-[1-bromo-meth-(E)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 41 percent / methanol; CH₂Cl₂ / 44 h / Ambient temperature

2: 1.) Tf₂O, Et₃N, 2.) aq. HCl / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

3: 1.) Ph₃P / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, -78 deg C, 30 min

4: 83 percent / Zn-Cu, NH₄Cl / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

With hydrogenchloride; trifluoromethylsulfonic anhydride; copper; ammonium chloride; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm970351x