Product Name

  • Name

    Faropenem sodium hemipentahydrate

  • EINECS 1312995-182-4
  • CAS No. 106560-14-9
  • Article Data3
  • CAS DataBase
  • Density 1.569 g/cm3
  • Solubility
  • Melting Point
  • Formula C12H15NO5S
  • Boiling Point 570.249 °C at 760 mmHg
  • Molecular Weight 285.321
  • Flash Point 298.676 °C
  • Transport Information
  • Appearance Light yellow powder
  • Safety
  • Risk Codes R20/21/22
  • Molecular Structure Molecular Structure of 106560-14-9 (Faropenem sodium hemipentahydrate)
  • Hazard Symbols
  • Synonyms 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, [5R-[3(R*),5a,6a(R*)]]-;(+)-(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid;(5R,6S,8R,2'R)-2-(2'-tetrahydrofuryl)-6-(1-hydroxyethyl)-2-penem-3-carboxylicacid;
  • PSA 112.37000
  • LogP 0.31160

Synthetic route

(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester
1004548-62-2

(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; sodium hydrogencarbonate; 5%-palladium/activated carbon In water; ethyl acetate at 20 - 30℃; under 4413.43 - 5149.01 Torr;
Stage #2: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran; water at 20 - 30℃; under 4413.43 - 5149.01 Torr; pH=7; Aqueous phosphate buffer;
Stage #2: With disodium hydrogenphosphate In tetrahydrofuran; water pH=6.8 - 7.0; Aqueous phosphate buffer;
Stage #3: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20 - 25℃; under 4413.43 - 5149.01 Torr; pH=7; Autoclave; Phosphate buffer; Inert atmosphere;
Stage #2: With hydrogenchloride; water pH=1.8 - 2.0; Product distribution / selectivity; Inert atmosphere;
R-(+)-thio tetrahydrofuran-2-carboxylic acid

R-(+)-thio tetrahydrofuran-2-carboxylic acid

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / acetone / 2 h / 0 - 20 °C / pH 8 - 10
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C
3: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
4: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one
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

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / acetone / 2 h / 0 - 20 °C / pH 8 - 10
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C
3: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
4: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
(R)-Tetrahydro-furan-2-carbothioic acid S-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl} ester
106560-32-1

(R)-Tetrahydro-furan-2-carbothioic acid S-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl} ester

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 0 - 5 °C
2: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
3: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
C25H34N2O9SSi

C25H34N2O9SSi

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
2: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
C25H34N2O7SSi

C25H34N2O7SSi

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 40℃; under 3040.2 Torr; for 16h;
C25H34N2O7SSi

C25H34N2O7SSi

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 40℃; under 3040.2 Torr; for 16h;

Conditions
ConditionsYield
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; sodium hydrogencarbonate; 5%-palladium/activated carbon In water; ethyl acetate at 20 - 30℃; under 4413.43 - 5149.01 Torr;
Stage #2: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran; water at 20 - 30℃; under 4413.43 - 5149.01 Torr; pH=7; Aqueous phosphate buffer;
Stage #2: With disodium hydrogenphosphate In tetrahydrofuran; water pH=6.8 - 7.0; Aqueous phosphate buffer;
Stage #3: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20 - 25℃; under 4413.43 - 5149.01 Torr; pH=7; Autoclave; Phosphate buffer; Inert atmosphere;
Stage #2: With hydrogenchloride; water pH=1.8 - 2.0; Product distribution / selectivity; Inert atmosphere;
(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester
1004548-62-2

(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; sodium hydrogencarbonate; 5%-palladium/activated carbon In water; ethyl acetate at 20 - 30℃; under 4413.43 - 5149.01 Torr;
Stage #2: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran; water at 20 - 30℃; under 4413.43 - 5149.01 Torr; pH=7; Aqueous phosphate buffer;
Stage #2: With disodium hydrogenphosphate In tetrahydrofuran; water pH=6.8 - 7.0; Aqueous phosphate buffer;
Stage #3: With hydrogenchloride In water for 1h; pH=1.8 - 2.0; Product distribution / selectivity;
Stage #1: (5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20 - 25℃; under 4413.43 - 5149.01 Torr; pH=7; Autoclave; Phosphate buffer; Inert atmosphere;
Stage #2: With hydrogenchloride; water pH=1.8 - 2.0; Product distribution / selectivity; Inert atmosphere;
R-(+)-thio tetrahydrofuran-2-carboxylic acid

R-(+)-thio tetrahydrofuran-2-carboxylic acid

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / acetone / 2 h / 0 - 20 °C / pH 8 - 10
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C
3: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
4: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one
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

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / acetone / 2 h / 0 - 20 °C / pH 8 - 10
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C
3: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
4: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
(R)-Tetrahydro-furan-2-carbothioic acid S-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl} ester
106560-32-1

(R)-Tetrahydro-furan-2-carbothioic acid S-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl} ester

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 0 - 5 °C
2: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
3: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
C25H34N2O9SSi

C25H34N2O9SSi

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Reflux
2: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol / 16 h / 40 °C / 3040.2 Torr
View Scheme
C25H34N2O7SSi

C25H34N2O7SSi

faropenem
106560-14-9

faropenem

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 40℃; under 3040.2 Torr; for 16h;
faropenem
106560-14-9

faropenem

A

(R)-5-(Tetrahydro-furan-2-yl)-thiazole-4-carboxylic acid

(R)-5-(Tetrahydro-furan-2-yl)-thiazole-4-carboxylic acid

B

4-Formyl-2-[4-hydroxy-but-(Z)-ylidene]-5-methyl-2,5-dihydro-thiophene-3-carboxylic acid

4-Formyl-2-[4-hydroxy-but-(Z)-ylidene]-5-methyl-2,5-dihydro-thiophene-3-carboxylic acid

C

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
754152-74-4

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

D

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
774505-06-5

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

Conditions
ConditionsYield
Product distribution; Ambient temperature; 0.1 M phosphate buffer (pH: 7.0), class C β-lactamase from Citrobacter freundii GN7391; other β-lactamases;
...Expand
faropenem
106560-14-9

faropenem

A

(R)-5-(Tetrahydro-furan-2-yl)-thiazole-4-carboxylic acid

(R)-5-(Tetrahydro-furan-2-yl)-thiazole-4-carboxylic acid

B

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
754152-74-4

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

C

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
774505-06-5

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

Conditions
ConditionsYield
Ambient temperature; 0.1 M phosphate buffer (pH: 7.0), class C β-lactamase from Citrobacter freundii;
Ambient temperature; 0.1 M phosphate buffer (pH: 7.0), class A β-lactamase from Bacillus cereus;
...Expand
faropenem
106560-14-9

faropenem

A

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
754152-74-4

(S)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

B

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid
774505-06-5

(R)-2-((1S,2R)-1-Carboxy-2-hydroxy-propyl)-5-[4-hydroxy-but-(Z)-ylidene]-2,5-dihydro-thiazole-4-carboxylic acid

Conditions
ConditionsYield
Ambient temperature; 0.1 M phosphate buffer (pH: 7.0), class A β-lactamase from Escherichia coli;
faropenem
106560-14-9

faropenem

Furopenem
122547-49-3

Furopenem

Conditions
ConditionsYield
With sodium 2-ethylhexanoic acid In tetrahydrofuran; water at 20℃; for 2h;125 g

Faropenemsodiumhemipentahydrate History

FDA rejects Replidyne’s faropenem Louisville firm drug rejected; considered “nonapprovable’ 10/24/06 The US Food and Drug Administration (FDA) refused to approve faropenem, an antibiotic manufactured by Louisville-based Replidyne. The FDA said the drug was “nonapprovable,” but did not refer to specific safety concerns about the product.The company will have to conduct new studies and clinical trials, lasting an estimated two more years, to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis and skin infections.

Faropenemsodiumhemipentahydrate Specification

The Faropenemsodiumhemipentahydrate, with the CAS registry number 106560-14-9, is also known as (+)-(5R,6S)-6-((1R)-1-hydroxyethyl)-7-oxo-3-((2R)-tetrahydro-2-furyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid. It belongs to the product category of API. This chemical's molecular formula is C12H15NO5S and molecular weight is 285.32. What's more, its systematic name is (5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid. This chemical is an orally-active beta-lactam antibiotic belonging to the penem group. It is resistant to some forms of extended-spectrum beta-lactamase.

Physical properties of Faropenemsodiumhemipentahydrate are: (1)ACD/LogP: -1.087; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.57; (4)ACD/LogD (pH 7.4): -4.30; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 112.37 Å2; (13)Index of Refraction: 1.668; (14)Molar Refractivity: 67.785 cm3; (15)Molar Volume: 181.807 cm3; (16)Polarizability: 26.872×10-24cm3; (17)Surface Tension: 76.44 dyne/cm; (18)Density: 1.569 g/cm3; (19)Flash Point: 298.676 °C; (20)Enthalpy of Vaporization: 98.247 kJ/mol; (21)Boiling Point: 570.249 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N1/C(=C(\S[C@@H]1[C@H]2[C@H](O)C)[C@@H]3OCCC3)C(=O)O
(2)Std. InChI: InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1
(3)Std. InChIKey: HGGAKXAHAYOLDJ-FHZUQPTBSA-N

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