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CAS No.: | 106560-14-9 |
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Name: | Faropenem sodium hemipentahydrate |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C12H15NO5S |
Molecular Weight: | 285.321 |
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; |
EINECS: | 1312995-182-4 |
Density: | 1.569 g/cm3 |
Boiling Point: | 570.249 °C at 760 mmHg |
Flash Point: | 298.676 °C |
Appearance: | Light yellow powder |
Risk Codes: | R20/21/22 |
PSA: | 112.37000 |
LogP: | 0.31160 |
(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid 4-nitrobenzyl ester
faropenem
Conditions | Yield |
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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; |
faropenem
Conditions | Yield |
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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
faropenem
Conditions | Yield |
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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
faropenem
Conditions | Yield |
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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 |
faropenem
Conditions | Yield |
---|---|
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 |
faropenem
Conditions | Yield |
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With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 40℃; under 3040.2 Torr; for 16h; |
Conditions | Yield |
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With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 40℃; under 3040.2 Torr; for 16h; |
Conditions | Yield |
---|---|
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
faropenem
Conditions | Yield |
---|---|
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; |
faropenem
Conditions | Yield |
---|---|
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 |
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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.
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