(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 25 - 30℃; for 5h; pH=8 - 8.5; | 90.85% |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With trimethylsilyl bromide In dichloromethane at 20 - 25℃; for 5.5h; | 89% |
diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With methoxybenzene; trifluoroacetic acid |
(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
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 |
diphenylmethyl (6R,7R)-7-(phenylacetamido)ceph-3-em-4-carboxylate
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) PCl5, Py, (ii) MeOH 2: PhOMe, CF3CO2H View Scheme |
(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
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: <(Ph3P)3Rh>Cl / benzene 2: (i) PCl5, Py, (ii) MeOH 3: PhOMe, CF3CO2H View Scheme |
p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
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 |
(6R,7R)-1-aza-3-chloro-7-amino-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
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 |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
ceftizoxime
Conditions | Yield |
---|---|
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% |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-[2-(trityl-amino)-thiazol-4-yl]-acetic acid
(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 | Yield |
---|---|
With pyridine; trichlorophosphate Substitution; | 96% |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
1-benzyl-4-fluoropyridinium bromide
C19H17N3O3S
Conditions | Yield |
---|---|
With sodium hydroxide In water at 22℃; pH 7; | 54% |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
diazodiphenylmethane
diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Conditions | Yield |
---|---|
In acetonitrile |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 96 percent / POCl3; pyridine 2.1: trifluoracetic acid / methoxybenzene / purified by chromatography and lyophilization 2.2: 81 percent / NaHCO3 View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: 63 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 99 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: 69 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 100 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: 62 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 86 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: 55 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 86 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-<2-(3-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetonitrile 2: 63 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-<2-(2-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetonitrile 2: 69 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-<2-(3-hydroxy-2-pyridyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetonitrile 2: 62 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetonitrile 2: 55 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme |
2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefotaxime sodium salt
Conditions | Yield |
---|---|
Stage #1: 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid With dmap; dicyclohexyl-carbodiimide In ethanol at 20℃; for 0.5h; Stage #2: With 1-hydroxy-pyrrolidine-2,5-dione In ethanol at 20℃; for 0.5h; Stage #3: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Further stages; | 2.59 g |
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
ceftizoxime
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In chloroform for 0.333333h; Stage #2: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate In chloroform at 35℃; for 4.5h; Temperature; | 87 g |
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
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.
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