(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

Base Information

Chemical Name:(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone
CAS No.:84692-00-2
Molecular Formula:C₁₉H₂₃NO₅S
Molecular Weight:377.461
Hs Code.:

Synonyms:(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

Chemical Property:

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Technology Process of (+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

There total 2 articles about (+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone 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: 51.0%

: 541-41-3
chloroformic acid ethyl ester

: 84691-99-6
(+/-)-(E)-1-ethoxycarbonylmethyl-4-(2-benzylthio)ethenyl-2-azetidinone

: 84692-00-2
(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

Guidance literature:: With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1248/cpb.30.3624

Reference yield:

: 84691-96-3,84691-97-4
1-ethoxycarbonylmethyl-4-(2-benzylsulfinyl)ethenyl-2-azetidinone

: 84692-00-2
(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / KI, acetyl chloride / dimethylformamide / 1.) 0 deg C, 30 min; 2.) 25 deg C, 30 min

2: 51 percent / n-BuLi, 1,1,1,3,3,3-hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C

With n-butyllithium; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; potassium iodide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.30.3624

Reference yield:

: 84692-00-2
(+/-)-(E)-1-bis(ethoxycarbonyl)methyl-4-(2-benzylthio)-ethyl-2-azetidinone

: 84692-02-4
(+/-)-diethyl 3-benzylthio-7-oxo-1-azabicyclo<3.2.0>hept-3-ene-2,2-bis(carboxylate)

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) Br₂, 2.) NaH / 1.) ether, 0-5 deg C, 15 min; 2.) DMF, 0-5 deg C, 1.5 h

2: DBU / tetrahydrofuran / 5 h / 24 °C

With bromine; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
DOI:10.1248/cpb.30.3624