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

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
Article Data12
CAS DataBase
Density 1.56 g/cm³
Solubility
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
Appearance White to off-white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 129.73000
LogP 0.64830

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 2524-64-3
chlorophosphoric acid diphenyl ester

: (S)-4-mercapto-2-oxoppyrrolidine

: 4-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[(R)-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester; chlorophosphoric acid diphenyl ester With N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Substitution; Stage #2: (S)-4-mercapto-2-oxoppyrrolidine With N-ethyl-N,N-diisopropylamine In acetonitrile for 1h; Substitution;	67%

...Expand

: 69739-34-0
t-butyldimethylsiyl triflate

: (E)-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanol

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: (5R,6S)-4-nitrobenzyl 6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-((E)-4-(hydroxymethyl)styryl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions

Conditions	Yield
Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: t-butyldimethylsiyl triflate In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #3: (E)-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanol With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In dichloromethane; water; N,N-dimethyl-formamide at -78 - 30℃; for 1h; Inert atmosphere;	59%

Yield

Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: t-butyldimethylsiyl triflate In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #3: (E)-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanol With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In dichloromethane; water; N,N-dimethyl-formamide at -78 - 30℃; for 1h; Inert atmosphere;

59%

...Expand

: 59016-93-2
p-hydroxymethylphenylboronic acid

: 79271-56-0
Triethylsilyl trifluoromethanesulfonate

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: (5R,6S)-4-nitrobenzyl 3-(4-(hydroxymethyl)phenyl)-7-oxo-6-((R)-1-((triethylsilyl)oxy)ethyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions

Conditions	Yield
Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: triethylsilyl trifluoromethyl sulfonate In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #3: p-hydroxymethylphenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In water; N,N-dimethyl-formamide at -78 - 30℃; for 1.5h; Inert atmosphere;	33%

Yield

Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: triethylsilyl trifluoromethyl sulfonate In dichloromethane at -78℃; for 1h; Inert atmosphere;
Stage #3: p-hydroxymethylphenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In water; N,N-dimethyl-formamide at -78 - 30℃; for 1.5h; Inert atmosphere;

33%

...Expand

: 358-23-6
trifluoromethylsulfonic anhydride

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 994-89-8
tributylethynyltin

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: (5R,6S)-3-Ethynyl-7-oxo-6-((R)-1-trimethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With diisopropylamine In tetrahydrofuran at -78℃; for 0.25h; Addition; Stage #2: trimethylsilyl trifluoromethanesulfonate With triethylamine In tetrahydrofuran at -78℃; for 0.333333h; Etherification; Stage #3: tributylethynyltin With trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0); zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at 20℃; for 2h; Addition; Stille coupling;	32%

Yield

Stage #1: trifluoromethylsulfonic anhydride; (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With diisopropylamine In tetrahydrofuran at -78℃; for 0.25h; Addition;
Stage #2: trimethylsilyl trifluoromethanesulfonate With triethylamine In tetrahydrofuran at -78℃; for 0.333333h; Etherification;
Stage #3: tributylethynyltin With trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0); zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at 20℃; for 2h; Addition; Stille coupling;

32%

...Expand

: 105675-99-8
cis-1-cyano-4-mercaptocyclohexane

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105693-26-3
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 20 h; Yield given. Multistep reaction;

: 105676-07-1
cis-3-mercaptocyclopentanecarboxamide

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105675-86-3, 105814-13-9
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 3 d; Yield given. Multistep reaction;

: 105676-08-2
cis-4-mercaptocyclohexanecarboxamide

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105675-88-5
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 3 d; Yield given. Multistep reaction;

: 105675-97-6
cis-3-mercapto-1-(p-nitrobenzyloxycarboxylamino)cyclopentane

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105676-04-8, 105814-12-8
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 20 h; Yield given. Multistep reaction;

: 105675-98-7
cis-4-mercapto-1-(p-nitrobenzyloxycarbonylamino)cyclohexane

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105675-87-4
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 6 d; Yield given. Multistep reaction;

: 105676-03-7
cis-4-(p-nitrobenzyloxycarbonylaminomethyl)cyclohexylthiol

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 105693-27-4
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 6 d; Yield given. Multistep reaction;

: 358-23-6
trifluoromethylsulfonic anhydride

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 135439-84-8
p-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-trifluoromethylsulphonyloxy-carbapen-2-em-3carboxylate

Conditions

Conditions	Yield
With diisopropylamine In tetrahydrofuran at -70℃; for 0.5h; Addition; Title compound not separated from byproducts;

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 75321-08-3
p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 1h; Addition;
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile

: 4124-41-8
p-toluenesulfonylanhydride

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 80735-70-2
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(toluene-4-sulfonyloxy)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -60 - 0℃;

: 186581-53-3, 908094-01-9
diazomethane

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; Methylation;

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-methoxy-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dioxane / 20 °C 2: H2 / 10 percent Pd/C / ethyl acetate / 0 °C 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

: (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / -60 - 0 °C 2: Et3N / CH2Cl2 / 12 h / -70 °C 3: 67 percent / Bu4N(+)Cl(-), K2CO3 / PdCl2(dppf) / tetrahydrofuran; H2O; CH2Cl2 / 1.67 h / 30 °C 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

: 226700-71-6
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-(toluene-4-sulfonyloxy)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / -60 - 0 °C 2: Et3N / CH2Cl2 / 12 h / -70 °C 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

: (5R,6S)-2-[(2S,4S)-2-carbamoyl-1,1-dimethylpyrrolidinio-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-diisopropylethylamine / acetonitrile / 1 h / 0 °C 2: N,N-diisopropylethylamine / acetonitrile 3: H2 / 10 percent Pd-C / tetrahydrofuran; aq. phosphate buffer / 2.5 h / 20 °C / pH 7 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

: (2S,4S)-2-Carbamoyl-4-[(5R,6S)-6-((R)-1-hydroxy-ethyl)-2-(4-nitro-benzyloxycarbonyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-1,1-dimethyl-pyrrolidinium

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diisopropylethylamine / acetonitrile / 1 h / 0 °C 2: N,N-diisopropylethylamine / acetonitrile 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

: 1026234-25-2
p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 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

: (5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thiazol-4-yl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C 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

: 1025902-20-8
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thiazol-5-yl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C 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

: 165743-32-8
p-Nitrobenzyl-(5R,6S)-6-[(1R)-hydroxyethyl]-2-(1-methylpyrazol-3-yl)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C 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

: 1025809-56-6
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 3 steps
1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C
1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C
1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C
2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C
3.1: Et3N / CH2Cl2; hexane / 1 h / 20 °C
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

: 1026821-85-1
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-isopropyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme

Yield

: 74288-40-7
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester

: 1025968-65-3
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-methoxymethyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C 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

: 165743-30-6
p-nitrobenzyl (5R,6S)-6-[(1R)-hydroxyethyl]-2-(1-phenylpyrazol-3-yl)-carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: 67 percent / Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C 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

: 204385-18-2
p-nitrobenzyl (5R,6S)-2-[3-(phenyl)isoxazol-5-yl]-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: 62 percent / Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme

Yield

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.

Product Name

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

Synthetic route

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

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

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

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