(5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Base Information

Chemical Name:(5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
CAS No.:75468-47-2
Molecular Formula:C₁₄H₁₂N₂O₅
Molecular Weight:288.26
Hs Code.:
Mol file:75468-47-2.mol

Synonyms:(5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Suppliers and Price of (5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Supply Marketing:

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

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Chemical Property of (5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Chemical Property:

PSA：92.43000
LogP:1.98760

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

There total 9 articles about (5S)-7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (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: 68.3%

: 87730-73-2,87730-74-3
p-nitrobenzyl <4(S)-(3-carbomenthyloxy-2-propen-1-yl)azetidin-2-on-1-yl>triphenylphosphoranylideneacetate

: 208192-14-7
menthyl glyoxylate hydrate

: 75468-47-2
p-nitrobenzyl 5(S)-carbapen-2-em-3-carboxylate

Guidance literature:: With dimethylsulfide; ozone; trifluoroacetic acid; In dichloromethane; 1.) -78 deg C, 5 min; 2.) 0 deg C to 5 deg C, 1 h;
DOI:10.1139/v83-391

Reference yield:

: 110-44-1,91751-55-2
sorbic Acid

: 75468-47-2
p-nitrobenzyl 5(S)-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 46.7 percent / conc. sulfuric acid / benzene / 120 h / Heating

2: 94.5 percent / 1.) diisopropylamine, n-butyllithium; 2.) hexamethylphosphoramide / tetrahydrofuran; hexane / 2 h / -78 °C

3: 28.4 percent / 2.) sodium sulfite, water / CH₂Cl₂ / 1.) rt., 24 h; 2.) 0 deg C to 5 deg C, pH: 7-9

4: 88.6 percent / 1,4-diazabicyclo<2.2.2>octane / acetonitrile / 168 h / Ambient temperature

5: benzene / 3 h / Heating

6: pyridine, thionyl chloride / tetrahydrofuran / 0.5 h / -15 °C

7: 2,6-lutidine / dioxane / 20 h / Ambient temperature

8: 68.3 percent / 1.) trifluoroacetic acid, ozone; 2.) dimethyl sulfide / CH₂Cl₂ / 1.) -78 deg C, 5 min; 2.) 0 deg C to 5 deg C, 1 h

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; thionyl chloride; dimethylsulfide; sulfuric acid; water; ozone; diisopropylamine; trifluoroacetic acid; sodium sulfite; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1139/v83-391

Reference yield:

: 87730-67-4
(-)-menthyl 2,4-hexadienoate

: 75468-47-2
p-nitrobenzyl 5(S)-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 94.5 percent / 1.) diisopropylamine, n-butyllithium; 2.) hexamethylphosphoramide / tetrahydrofuran; hexane / 2 h / -78 °C

2: 28.4 percent / 2.) sodium sulfite, water / CH₂Cl₂ / 1.) rt., 24 h; 2.) 0 deg C to 5 deg C, pH: 7-9

3: 88.6 percent / 1,4-diazabicyclo<2.2.2>octane / acetonitrile / 168 h / Ambient temperature

4: benzene / 3 h / Heating

5: pyridine, thionyl chloride / tetrahydrofuran / 0.5 h / -15 °C

6: 2,6-lutidine / dioxane / 20 h / Ambient temperature

7: 68.3 percent / 1.) trifluoroacetic acid, ozone; 2.) dimethyl sulfide / CH₂Cl₂ / 1.) -78 deg C, 5 min; 2.) 0 deg C to 5 deg C, 1 h

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; thionyl chloride; dimethylsulfide; water; ozone; diisopropylamine; trifluoroacetic acid; sodium sulfite; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1139/v83-391