CAS No.122547-49-3,Faropenem sodium Suppliers

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Basic Information

Molecular Structure:
CAS No.:	122547-49-3
Name:	Faropenem sodium
Article Data:	5

Formula:	C₁₂H₁₄NNaO₅S
Molecular Weight:	307.303
Synonyms:	4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, monosodium salt,[5R-[3(R),5a,6a(R)]]-;4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, monosodium salt,(5R,6S)- (9CI);(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-2-tetrahydrofuryl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid sodium salt;ALP 201;Farom;Fropenem;Furopenem;SY 5555;Wy 49605;Sun 5555;
EINECS:	1592732-453-0
Boiling Point:	570.2 °C at 760 mmHg
Flash Point:	298.7 °C
Appearance:	pale yellow crystals
PSA:	115.20000
LogP:	-1.02310

Synthetic route

: 106559-80-2
(5R,6S)-6-((R)-1-hydroxyethyl)-2-((R)-tetrahydro-2-furyl)penem-3-carboxylic acid allyl ester

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium 2-ethylhexanoic acid In water; ethyl acetate at 20℃; for 5h; Inert atmosphere; Large scale reaction;	86.5%
Stage #1: (5R,6S)-6-((R)-1-hydroxyethyl)-2-((R)-tetrahydro-2-furyl)penem-3-carboxylic acid allyl ester With sodium isooctanoate; sodium caprylate; triphenylphosphine In dichloromethane; ethyl acetate at 20℃; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In dichloromethane; ethyl acetate at 25 - 30℃; for 0.666667h; Inert atmosphere;	73.3%
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; sodium 2-ethylhexanoic acid In ethyl acetate for 1h; Ambient temperature;

: 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

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. NaHCO3 / acetone / 4 h / 60 °C 2: Et3N / CH2Cl2 / 0.17 h / -20 °C 3: triethyl phosphite / xylene / 11 h / Heating 4: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C 5: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature View Scheme
Multi-step reaction with 5 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 5: sodium 2-ethylhexanoic acid / tetrahydrofuran; water / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: aq. NaHCO3 / acetone / 4 h / 60 °C
2: Et3N / CH2Cl2 / 0.17 h / -20 °C
3: triethyl phosphite / xylene / 11 h / Heating
4: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C
5: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature
View Scheme

Multi-step reaction with 5 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
5: sodium 2-ethylhexanoic acid / tetrahydrofuran; water / 2 h / 20 °C
View Scheme

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

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. NaHCO3 / acetone / 4 h / 60 °C 2: Et3N / CH2Cl2 / 0.17 h / -20 °C 3: triethyl phosphite / xylene / 11 h / Heating 4: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C 5: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature View Scheme
Multi-step reaction with 5 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 5: sodium 2-ethylhexanoic acid / tetrahydrofuran; water / 2 h / 20 °C View Scheme

Yield

: 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

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / CH2Cl2 / 0.17 h / -20 °C 2: triethyl phosphite / xylene / 11 h / Heating 3: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C 4: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature View Scheme
Multi-step reaction with 4 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 4: sodium 2-ethylhexanoic acid / tetrahydrofuran; water / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 3 h / -20 - -15 °C 2: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 4.5 h / 150 °C 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 30 °C 4: palladium 10% on activated carbon; sodium hydrogencarbonate; hydrogen / ethyl acetate; water / 16 h / 25 - 35 °C View Scheme

: 120705-67-1
allyl (5R,6S)-6((R)-1-t-butyldimethylsilyloxyethyl)-7-oxo-3-((R)-2-tetrahydrofuryl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C 2: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature View Scheme

: 429691-43-0
(3S,4R)-1-(allyloxy)oxoacetyl-3-((R)-1-hydroxyethyl)-4-((R)-2-tetrahydrofuranyl)carbonylthio-azetidin-2-one

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethyl phosphite / xylene / 11 h / Heating 2: AcOH, tetra-n-butylammonium fluoride / tetrahydrofuran / 8.5 h / 50 °C 3: Ph3P, tetrakis(triphenylphosphine)palladium, sodium 2-ethylhexanoate / ethyl acetate / 1 h / Ambient temperature View Scheme

: 106560-14-9
faropenem

: 122547-49-3
Furopenem

Conditions

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

: C25H34N2O9SSi

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3: sodium 2-ethylhexanoic acid / tetrahydrofuran; water / 2 h / 20 °C View Scheme

: C19H21NO5S

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In water; ethyl acetate at 25 - 35℃; for 16h;

: C25H35NO7SSi

: 122547-49-3
Furopenem

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethyl phosphite / 5,5-dimethyl-1,3-cyclohexadiene / 4.5 h / 150 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 30 °C 3: palladium 10% on activated carbon; sodium hydrogencarbonate; hydrogen / ethyl acetate; water / 16 h / 25 - 35 °C View Scheme

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Chemistry

IUPAC Name: Sodium(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(oxolan-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Molecular Weight: 307.29803 [g/mol]
Molecular Formula: C₁₂H₁₄NNaO₅S
H-Bond Donor: 1
H-Bond Acceptor: 5
Flash Point: 298.7 °C
Enthalpy of Vaporization: 98.25 kJ/mol
Boiling Point: 570.2 °C at 760 mmHg
Vapour Pressure: 2.23E-15 mmHg at 25 °C
Classification Code of Sun 5555 (CAS NO.122547-49-3): Drug / Therapeutic Agent; Reproductive Effect

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	oral	> 3gm/kg (3000mg/kg)		Chemotherapy Vol. 42(Suppl,
dog	LD50	intravenous	> 1200mg/kg (1200mg/kg)		Drugs of the Future. Vol. 18, Pg. 525, 1993.
mouse	LD50	intravenous	3300mg/kg (3300mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD KIDNEY, URETER, AND BLADDER: INCONTINENCE	Chemotherapy Vol. 42(Suppl,
mouse	LD50	oral	> 2gm/kg (2000mg/kg)		Drugs of the Future. Vol. 18, Pg. 525, 1993.
rat	LD50	oral	> 2gm/kg (2000mg/kg)		Drugs of the Future. Vol. 18, Pg. 525, 1993.
rat	LDLo	intravenous	800mg/kg (800mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25, Pg. 1781, 1997.

Specification

Sun 5555 (CAS NO.122547-49-3), its Synonyms are (5R,6S)-6-(1(R)-Hydroxyethyl)-2-(2(R)-tetrahydrofuryl)penem-3-carboxylic acid monosodium salt ; ALP 201 ; CCRIS 6723 ; Fropenum sodium ; 4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, monosodium salt, (5R-(3(R*),5-alpha,6-alpha(R*)))- .