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P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate
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Name

P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

 EINECS 616-072-7
CAS No. 74288-40-7 Density 1.56 g/cm3
PSA 129.73000 LogP 0.64830
Solubility N/A Melting Point 108-110oC
Formula C16H16N2O7 Boiling Point 607.5 °C at 760 mmHg
Molecular Weight 348.312 Flash Point 321.2 °C
Transport Information N/A Appearance White to off-white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 74288-40-7 (p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate) Hazard Symbols N/A
Synonyms

1-Azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(1-hydroxyethyl)-3,7-dioxo-, (4-nitrophenyl)methyl ester, [5R-[5a,6a(R*)]]-;ADC 13;p-Nitrobenzyl(5R,6S)-6-((1R)-1-hydroxyethyl)-2-oxocarbapenam-3-carboxylate;p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate;

Article Data 12

P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate Synthetic route

74288-39-4

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
With dirhodium tetraacetate In toluene at 80℃; for 2.5h; Cyclization;
rhodium (II) octanoate dimer In dichloromethane for 4 - 5h; Heating / reflux;
With nitrogen; rhodium(II) acetate In benzene

rhodium(II) acetate

74288-39-4

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
In toluene

(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2one

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
With nitrogen; rhodium(II) acetate In benzene
1180012-46-7

(3S,4R)-benzyl N-(p-toluenesulfonyl)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: samarium diiodide; samarium; isopropyl alcohol
2: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran
3: lead(IV) tetraacetate / N,N-dimethyl-formamide
4: zinc(II) chloride / dichloromethane
5: hydrogenchloride; methanol
6: dirhodium tetraacetate / toluene
View Scheme
1180012-50-3

(3S,4R)-benzyl 3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran
2: lead(IV) tetraacetate / N,N-dimethyl-formamide
3: zinc(II) chloride / dichloromethane
4: hydrogenchloride; methanol
5: dirhodium tetraacetate / toluene
View Scheme
76899-07-5, 78963-47-0, 78963-48-1, 78963-60-7, 80951-41-3, 81275-02-7, 85647-75-2, 85954-95-6, 92217-74-8, 104527-11-9, 76855-69-1

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / dichloromethane
2: hydrogenchloride; methanol
3: dirhodium tetraacetate / toluene
View Scheme
93788-48-8

4-nitrobenzyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / dichloromethane
2: hydrogenchloride; methanol
3: dirhodium tetraacetate / toluene
View Scheme
115936-64-6

(3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidin-2-carboxylic acid

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lead(IV) tetraacetate / N,N-dimethyl-formamide
2: zinc(II) chloride / dichloromethane
3: hydrogenchloride; methanol
4: dirhodium tetraacetate / toluene
View Scheme
93861-39-3

(3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one

74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; methanol
2: dirhodium tetraacetate / toluene
View Scheme
74288-40-7

(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

623-51-8

ethyl 2-sulfanylacetate

(5R,6S)-4-nitrobenzyl 3-((2-ethoxy-2-oxoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions
ConditionsYield
Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester In acetonitrile at 0℃; for 0.75h;
Stage #2: ethyl 2-sulfanylacetate With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 1h;		74%

P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate Chemical Properties

Molecular Structure of P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (CAS NO.74288-40-7):

Empirical Formula: C16H16N2O7 
Molecular Weight: 348.3074 
Index of Refraction:  1.631 
Surface Tension:  71.9 dyne/cm 
Density:  1.5 g/cm3 
Flash Point:  317.4 °C 
Enthalpy of Vaporization:  94.09 kJ/mol 
Boiling Point:  601.3 °C at 760 mmHg 
Vapour Pressure:  2.63E-15 mmHg at 25°C 
Product Categories: (intermediate of imipenem,panipenem);Intermediates & Fine Chemicals; Pharmaceuticals

P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate Uses

 The usage of P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (CAS NO.74288-40-7) is as imipenem intermediate.

P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate Specification

 P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate ,its cas register number is 73323-65-6. It also can be called 1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(1-hydroxyethyl)-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)- ; 1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)- ; (1'R,5R,6S)-6-(1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester and so on.

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