• Name

  NITROCEFIN

• EINECS
• CAS No. 41906-86-9
• Article Data3
• CAS DataBase
• Density 1.67g/cm3
• Solubility DMSO (Slightly), Methanol (Slightly)
• Melting Point 103-113° (dec); mp 167-169° (dec) (Lee)
• Formula C₂₁H₁₆N₄O₈S₂
• Boiling Point 872oC at 760 mmHg
• Molecular Weight 516.512
• Flash Point 481.2oC
• Transport Information
• Appearance Orange to Red Solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Nitrocefin [BAN];5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid,3-[(1E)-2-(2,4-dinitrophenyl)- ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-,(6R,7R)-;(6R-(3(E),6alpha,7beta))-3-(2-(2,4-Dinitrophenyl)ethenyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;(7R)-3-((E)-2,4-Dinitrostyryl)-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid;Nitrocefin;
• PSA 231.89000
• LogP 4.10510

Synthetic route

C34H26N4O8S2

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
With methoxybenzene; trifluoroacetic acid In dichloromethane at 0℃; for 0.5h;	87%

39098-97-0

2-thienylacetic acid chloride

(6R,7R)-7-Amino-3-[(E)-2-(2,4-dinitro-phenyl)-vinyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
With N,N'-bis(trimethylsilyl)urea; ammonium bromide 1.) CH2Cl2, reflux, 1.5 h, 2.) CH2Cl2, -10 deg C, 1.5 h; Yield given. Multistep reaction;

(6R,7R)-3-[(Z)-2,4-dinitrostyryl]-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
In chloroform; dimethyl sulfoxide at 20℃; for 24h;	120 mg

p-methoxybenzyl (6R,7R)-3-(2,4-dinitrostyryl)-7-(2-thienylacetamido)-3-cephem-4-carboxylate

A

41906-86-9

Nitrocefin

B

(6R,7R)-3-[(Z)-2,4-dinitrostyryl]-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
With methoxybenzene; trifluoroacetic acid In dichloromethane for 0.25h; cooling; Title compound not separated from byproducts;

39098-97-0

2-thienylacetic acid chloride

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 78 percent / potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / 20 °C 2.1: sodium iodide / butan-2-one / 20 °C 3.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 3.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 4.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling View Scheme
Multi-step reaction with 5 steps 1.1: 78 percent / potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / 20 °C 2.1: sodium iodide / butan-2-one / 20 °C 3.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 3.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 4.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling 5.1: 120 mg / CHCl3; dimethylsulfoxide / 24 h / 20 °C View Scheme

101182-25-6

(6R,7R)-4-methoxybenzyl-3-(chloromethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium iodide / butan-2-one / 20 °C 2.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 2.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 3.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling View Scheme
Multi-step reaction with 4 steps 1.1: sodium iodide / butan-2-one / 20 °C 2.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 2.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 3.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling 4.1: 120 mg / CHCl3; dimethylsulfoxide / 24 h / 20 °C View Scheme

para-methoxybenzyl (6R,7R)-7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 78 percent / potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / 20 °C 2.1: sodium iodide / butan-2-one / 20 °C 3.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 3.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 4.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling View Scheme
Multi-step reaction with 5 steps 1.1: 78 percent / potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / 20 °C 2.1: sodium iodide / butan-2-one / 20 °C 3.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 3.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 4.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling 5.1: 120 mg / CHCl3; dimethylsulfoxide / 24 h / 20 °C View Scheme

p-methoxybenzyl (6R,7R)-3-(2,4-dinitrostyryl)-7-(2-thienylacetamido)-3-cephem-4-carboxylate

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling 2: 120 mg / CHCl3; dimethylsulfoxide / 24 h / 20 °C View Scheme

[(6R,7R)-2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 1.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 2.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling View Scheme
Multi-step reaction with 3 steps 1.1: potassium trimethylsilanolate / CH2Cl2; acetonitrile / 1 h / -10 °C 1.2: 0.90 g / CH2Cl2; acetonitrile / 5 h / -10 - 20 °C 2.1: trifluoroacetic acid; anisole / CH2Cl2 / 0.25 h / cooling 3.1: 120 mg / CHCl3; dimethylsulfoxide / 24 h / 20 °C View Scheme

957-68-6

7-Aminocephalosporanic acid

41906-86-9

Nitrocefin

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1.1: water; sodium hydroxide / methanol / -20 - -10 °C 2.1: sodium hydroxide / acetone; water / 0 °C / pH 8 2.2: 0.5 h 3.1: phosphorus tribromide / tetrahydrofuran / -5 °C / Inert atmosphere 4.1: ethyl acetate / 15 h / 20 °C 5.1: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C 6.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C View Scheme

15690-38-7

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / acetone; water / 0 °C / pH 8 1.2: 0.5 h 2.1: phosphorus tribromide / tetrahydrofuran / -5 °C / Inert atmosphere 3.1: ethyl acetate / 15 h / 20 °C 4.1: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C 5.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C View Scheme

29126-13-4

3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: phosphorus tribromide / tetrahydrofuran / -5 °C / Inert atmosphere 2: ethyl acetate / 15 h / 20 °C 3: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C 4: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C View Scheme

30361-56-9

(6R)-3-bromomethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

41906-86-9

Nitrocefin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate / 15 h / 20 °C 2: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C 3: methoxybenzene; trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C View Scheme

oxacillin bound N146K/E150K double mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

oxacillin bound N146K/E150K double mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

41906-86-9

Nitrocefin

nitrocefin complexed with oxacillin bound N146K/E150K double mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

nitrocefin complexed with oxacillin bound N146K/E150K double mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

Conditions

Conditions	Yield
In aq. buffer at 20℃; for 0.166667h; pH=7; Kinetics;

oxacillin bound N146K/E150K/H351N triple mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

oxacillin bound N146K/E150K/H351N triple mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

41906-86-9

Nitrocefin

nitrocefin complexed with oxacillin bound N146K/E150K/H351N triple mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

nitrocefin complexed with oxacillin bound N146K/E150K/H351N triple mutant variant of penicillin binding protein 2a (residues 23-668) from staphylococcus aureus ATCC 700699

Conditions

Conditions	Yield
In aq. buffer at 20℃; for 0.166667h; pH=7; Kinetics;

41906-86-9

Nitrocefin

C21H18N4O9S2

Conditions

Conditions	Yield
With β-lactamase Enzymatic reaction;