4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-, (4-nitrophenyl)methyl ester

Base Information

Chemical Name:4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-, (4-nitrophenyl)methyl ester
CAS No.:70389-05-8
Molecular Formula:C23H20N4O9S2
Molecular Weight:560.565
Hs Code.:

4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,
3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-,
(4-nitrophenyl)methyl ester

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Chemical Property of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-, (4-nitrophenyl)methyl ester

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Technology Process of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-, (4-nitrophenyl)methyl ester

There total 7 articles about 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-, (4-nitrophenyl)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: 69.0%

: 77705-10-3
{2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

: 70389-05-8
3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With hydroquinone; In xylene; at 130 - 135 ℃; for 10h;
DOI:10.1248/cpb.28.3232

Reference yield:

: 70389-04-7
(Z)-2-bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-3-(4-oxo-azetidin-2-ylsulfanyl)-acrylic acid 4-nitro-benzyl ester

: 70389-05-8
3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With copper(I) bromide dimethylsulfide complex; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/ja00502a051

Reference yield:

: 65750-59-6
2-(4-nitrobenzyloxycarbonylamino)ethanethiol

: 70389-05-8
3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) sodium methoxide; 2.) 4-acetoxy-2-azetidinone / 1.) MeOH; 2.) MeOH, -10 to 0 deg C

2: 95 percent / benzene; tetrahydrofuran / 5 h / Heating

3: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / -15 °C

4: 2,6-lutidine / tetrahydrofuran / 7.5 h / 70 °C

5: 69 percent / hydroquinone / xylene / 10 h / 130 - 135 °C

With 2,6-dimethylpyridine; thionyl chloride; 4-acetoxy azetidinone; sodium methylate; hydroquinone; In tetrahydrofuran; xylene; benzene;
DOI:10.1248/cpb.28.3232