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Basic Information
CAS No.: 36923-17-8
Name: 7-Amino-3-cephem-4-carboxylic acid
Article Data: 8
Molecular Structure:
Molecular Structure of 36923-17-8 (7-Amino-3-cephem-4-carboxylic acid)
Formula: C7H8N2O3S
Molecular Weight: 200.218
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R-trans)-;7b-Amino-3-cephem-4-carboxylicacid;Ceph-3-em-4-carboxylic acid, 7b-amino-;
EINECS: 609-312-7
Density: 1.699g/cm3
Melting Point: 215-218°C
Boiling Point: 536.9 °C at 760 mmHg
Flash Point: 278.5 °C
PSA: 108.93000
LogP: -0.16450
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Synthetic route

C7H9IN2O3S

36923-17-8

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

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 25 - 30℃; for 5h; pH=8 - 8.5;90.85%

C14H13N3O5S*ClH

36923-17-8

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

Conditions
ConditionsYield
With trimethylsilyl bromide In dichloromethane at 20 - 25℃; for 5.5h;89%
36923-21-4

diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

36923-17-8

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

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
35246-64-1

(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

36923-17-8

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: (PhCO)2O / dimethylsulfoxide / Ambient temperature
2: <(Ph3P)3Rh>Cl / benzene
3: (i) PCl5, Py, (ii) MeOH
4: PhOMe, CF3CO2H
View Scheme
36923-19-0

diphenylmethyl (6R,7R)-7-(phenylacetamido)ceph-3-em-4-carboxylate

36923-17-8

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) PCl5, Py, (ii) MeOH
2: PhOMe, CF3CO2H
View Scheme
35246-65-2

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

36923-17-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: <(Ph3P)3Rh>Cl / benzene
2: (i) PCl5, Py, (ii) MeOH
3: PhOMe, CF3CO2H
View Scheme
53116-50-0

p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate

36923-17-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diphenylsilyl chloride; aluminum (III) chloride / dichloromethane / 4 h / 15 - 25 °C
2.1: diisooctyl phenyl phosphite; bromine; 1H-imidazole / dichloromethane / 5 h / -45 - -40 °C
2.2: 0.5 h
3.1: trimethylsilyl bromide / dichloromethane / 5.5 h / 20 - 25 °C
View Scheme
53994-69-7

(6R,7R)-1-aza-3-chloro-7-amino-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

36923-17-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; ammonium hydroxide / water; methanol / 0.5 h / 15 - 25 °C / pH 7 - 7.5
2: sodium iodide; glycine; sodium hydrogencarbonate / acetone / 4 h / 25 - 30 °C / Sonication
3: potassium hydroxide / water; methanol / 5 h / 25 - 30 °C / pH 8 - 8.5
View Scheme
36923-17-8

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

C13H10N4O2S3

68401-81-0

ceftizoxime

Conditions
ConditionsYield
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With dmap In dichloromethane at -8 - 0℃;
Stage #2: C13H10N4O2S3 With dmap In dichloromethane at -5 - 0℃; for 0.25h; Reagent/catalyst; Temperature;		97%
36923-17-8

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

159048-31-4

{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-[2-(trityl-amino)-thiazol-4-yl]-acetic acid

1026067-63-9

(6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With pyridine; trichlorophosphate Substitution;96%
Raw Materials
35246-64-1
36923-21-4
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Chemistry

Product Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R,7R)-
Systematic of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R,7R)- (CAS NO.36923-17-8): 7-Amino-3-cephem-4-carboxylic acid ; 7-Amino-3-nor-3-cephem-4-carboxylic acid; 7-Amino-3-norcephalosporanic acid
CAS NO: 36923-17-8
Molecular Formula of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R,7R)- (CAS NO.36923-17-8): C7H8N2O3S
Molecular Weight: 200.21
Molecular Structure:

Melting Point: 111-113°C
ProductCategories: Organic acids 
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 2
Polar Surface Area: 108.93 Å2
Index of Refraction: 1.735
Molar Refractivity: 47.294 cm3
Molar Volume: 117.836 cm3
Surface Tension: 93.996 dyne/cm
Density of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R,7R)- (CAS NO.36923-17-8): 1.699 g/cm3
Flash Point: 278.508 °C
Enthalpy of Vaporization: 89.001 kJ/mol
Boiling Point: 536.902 °C at 760 mmHg

Uses

 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-, (6R,7R)- (CAS NO.36923-17-8) is used as cephalosporin butan, ceftizoxime intermediate.