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106560-14-9

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106560-14-9 Usage

Description

Farom was launched in Japan for use as an antibiotic against common respiratory tract pathogens. It can be prepared by several related routes of about seven steps starting with tetrahydrofuran-2-thiocarboxylic acid and a silylated azetidinone. It is a broad spectrum oral penem antibiotic that is β-lactamase stable. Farom is the most active β-lactam against anaerobes (more than cefaclor, cefixime and amoxicillin) but also has activity against Gram-positive, Gram-negative and enterobacteriaceae. It is equally active against strains carrying plasmid and chromosome mediated β-lactamases. The short plasma elimination half-life is the result of hydrolysis by renal dehydropeptidase. It is more stable to hydrolysis by extended spectrum β-lactamases than some second and third generation cephalosporins.

Originator

Suntory (Japan)

Uses

Different sources of media describe the Uses of 106560-14-9 differently. You can refer to the following data:
1. Faropenem (cas# 106560-14-9) is a compound useful in organic synthesis.
2. Treatmentof bacterial infections.

Brand name

Farom

Antimicrobial activity

An orally active penem with a broad spectrum of antibacterial activity, including activity against selected anaerobic pathogens. Although it is active against most enterobacteria, it has reduced activity against Ser. marcescens, Enterobacter spp. and some Providencia spp. It generally retains activity against many Gram-positive organisms, but has no useful activity against Ps. aeruginosa. It has reduced activity against E. faecium, methicillin-resistant Staph. aureus (MRSA) and some strains of coagulase-negative staphylococci. It is stable to hydrolysis by extended spectrum β-lactamases, but is hydrolyzed by carbapenemases. Esterified prodrugs with increased bioavailability have been studied in clinical trials but have not received regulatory approval.

Check Digit Verification of cas no

The CAS Registry Mumber 106560-14-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,5,6 and 0 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 106560-14:
(8*1)+(7*0)+(6*6)+(5*5)+(4*6)+(3*0)+(2*1)+(1*4)=99
99 % 10 = 9
So 106560-14-9 is a valid CAS Registry Number.
InChI:InChI=1/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

106560-14-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 6α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid

1.2 Other means of identification

Product number -
Other names faropenem free acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106560-14-9 SDS

106560-14-9Synthetic 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
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
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;
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;
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

106560-14-9Downstream Products

106560-14-9Relevant articles and documents

A synthesis method of faropenem sodium

-

Paragraph 0015; 0036; 0037, (2017/07/14)

The invention provides a method for synthesizing faropenem sodium. According to the method, oxalic acid chloride p-nitrobenzyl ester is used for replacing allyloxy oxalyl chloride in a conventional process, and thus the generation of polymer impurities is effectively prevented, and the raw material conversion rate and the product yield are increased; by adopting a method of catalytic hydrogenation under an acidic condition, silylation protection groups and p-nitrobenzyl ester protection groups are removed, organophosphorus impurities which are difficult to treat are effectively prevented, the separation and purification of products are facilitated, the maneuverability is improved, and the industrialized production is facilitated.

SOUP FAROPENEM FREE ACID

-

Page/Page column 7-8, (2008/06/13)

The present invention provides solid form of faropenem free acid, its hydrates and processes for their preparation thereof. Thus, for example, dissolving an alkali metal salt of faropenem in water, adjusting the pH of the solution formed with an acid to below about 2.5 and collecting the precipitated solid to obtain solid faropenem free acid.

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