Methyltriphenylphosphonium bromide
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 25℃; for 1.5h; pH=7 - 9; Temperature; Reagent/catalyst; Solvent; | 96.1% |
7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With acetic acid In phenol at 35℃; for 6h; Temperature; Reagent/catalyst; | 93.8% |
With sodium carbonate; penicillin G amidase In water at 29 - 33℃; pH=8; Large scale reaction; Enzymatic reaction; | 5.36 kg |
With penicillin acylase; sodium hydroxide at 30 - 32℃; pH=6.8 - 7.5; Reagent/catalyst; Temperature; Enzymatic reaction; |
7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With SO42-/SnO2-ZnO4 In acetonitrile at 50℃; for 1h; Solvent; Reagent/catalyst; | 82% |
With phosphoric acid; phenol at 40 - 50℃; Reagent/catalyst; | 22.8 g |
(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: nitric acid; sodium bromide / acetone / 3 h / 40 °C 2: potassium carbonate; sodium hydroxide / 2 h / 0 - 10 °C 3: methanol / 1 h / Reflux 4: acetic acid / phenol / 6 h / 35 °C View Scheme |
(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
(6R,7R)-7-amino-3-vinyl-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 iodide; triphenylphosphine; sodium hydroxide / dichloromethane; acetone; water / 10.5 h / 20 °C / pH 7-9 2: phosphoric acid; phenol / 2 h / 40 - 50 °C 3: penicillin acylase; sodium hydroxide / 30 - 32 °C / pH 6.8 - 7.5 / Enzymatic reaction View Scheme |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: C5H3N3O2S; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid at 0 - 32℃; for 1h; Stage #2: With sulfuric acid In water at 20 - 25℃; for 0.5h; pH=5; Temperature; | 98% |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydrogensulfite; triethylamine In tetrahydrofuran; water at 10 - 15℃; for 5h; | 96.1% |
(6R,7R)-7-amino-3-vinyl-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-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate Substitution; | 96% |
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefdinir
Conditions | Yield |
---|---|
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran at 20 - 23℃; for 5h; Stage #2: With hydrogenchloride; methoxybenzene In tetrahydrofuran; dichloromethane at -25 - -20℃; for 1.5h; | 88.6% |
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran; water at 20℃; for 4 - 6h; Stage #2: With potassium carbonate In water at 20℃; for 0.5 - 0.75h; pH=8.0 - 8.2; Stage #3: With sulfuric acid In water pH=2 - 2.5; | |
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid In tetrahydrofuran for 0.166667h; Stage #2: With water; triethylamine In tetrahydrofuran; dichloromethane at 15 - 25℃; for 3 - 4h; Stage #3: With sulfuric acid; water In tetrahydrofuran; dichloromethane at 35 - 40℃; for 2h; pH=2.4 - 2.5; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate
cefdinir
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate With triethylamine In N,N-dimethyl acetamide at 15 - 20℃; for 4h; Stage #2: With hydrogenchloride; methoxybenzene In dichloromethane; N,N-dimethyl acetamide at -15 - -10℃; for 2h; | 85.8% |
acetic acid tert-butyl ester
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 20℃; for 6h; Reagent/catalyst; Cooling with ice; | 77.7% |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide at 20℃; Cooling; | 25% |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetic acid
Conditions | Yield |
---|---|
Stage #1: 2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetic acid With phosphorus pentachloride In dichloromethane at -15 - -10℃; for 0.5h; Stage #2: (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With N-Trimethylsilylacetamide In dichloromethane at 25 - 27℃; for 10h; Stage #3: With water; trifluoroacetic acid at 12 - 15℃; for 4h; Further stages.; | 8.6% |
N,N'-bis(trimethylsilyl)urea
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Ambient temperature; |
cyclohexanone
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With hydrogen bromide In acetonitrile at 0℃; Yield given; |
acetone
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In acetic acid at 0℃; for 0.5h; Yield given; |
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
C16H15N5O6S2
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 15 - 20℃; for 6h; |
triethylamine
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 18 - 20℃; for 5h; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
N-Trimethylsilylacetamide
Conditions | Yield |
---|---|
With N,N-dimethyl acetamide at 25 - 30℃; for 0.5h; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-[(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dimethylformamide / Ambient temperature 2: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C 3: dimethylformamide; CH2Cl2; H2O; pyridine / 15 h 4: 98percent formic acid / 2 h / Ambient temperature View Scheme |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dimethylformamide / Ambient temperature 2: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C 3: dimethylformamide; CH2Cl2; H2O; pyridine / 15 h View Scheme |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylformamide / Ambient temperature 2: pyridine; dimethylformamide / 0.5 h / -10 - -5 °C View Scheme |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefdinir
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 3.5h; |
N,O-bis-(trimethylsilyl)-acetamide
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
In dichloromethane at 10 - 25℃; for 1h; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In water at 30 - 35℃; for 2h; Product distribution / selectivity; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
triethylamine
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 4℃; for 6h; |
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefdinir potassium
Conditions | Yield |
---|---|
Stage #1: syn-2-(2-aminothiazol-4-yl)-2-(methylcarbonyloxyimino)acetic acid mercaptobenzothiazolyl ester; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid In tetrahydrofuran; water at 15 - 20℃; pH=8.0 - 8.2; Stage #2: With water; potassium carbonate; ammonium chloride at 5 - 25℃; pH=8.0 - 8.2; Product distribution / selectivity; |
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-(Z)-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetimido]-3-vinyl-3-cephem-4-carboxylic acid cesium salt
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran; water at 15 - 20℃; pH=8.0 - 8.2; Stage #2: With ammonium chloride; caesium carbonate In water at 20 - 25℃; pH=7.8 - 8.2; Product distribution / selectivity; |
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-(Z)-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetimido]-3-vinyl-3-cephem-4-carboxylic acid cesium salt
Conditions | Yield |
---|---|
Stage #1: syn-2-(2-aminothiazol-4-yl)-2-(methylcarbonyloxyimino)acetic acid mercaptobenzothiazolyl ester; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran; dichloromethane; water at 15 - 25℃; for 0.5h; pH=~ 8.0 - 8.2; Stage #2: With water; ammonium chloride; caesium carbonate at 20 - 25℃; pH=7.8 - 8.2; Product distribution / selectivity; |
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
potassium 7-(Z)-[2-(2-aminothiazol-4-yl)-2-hydroxylminoacetimido]-3-vinyl-3-cephem-4-carboxylate
Conditions | Yield |
---|---|
Stage #1: syn-2-(2-aminothiazol-4-yl)-2-(methylcarbonyloxyimino)acetic acid mercaptobenzothiazolyl ester; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran; dichloromethane; water at 15 - 25℃; for 0.5h; pH=~ 8.0 - 8.2; Stage #2: With water; potassium carbonate; ammonium chloride at 20 - 25℃; pH=8.0 - 8.2; Product distribution / selectivity; |
thiourea
(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 20℃; for 4h; Stage #2: C7H7Cl2NO5 In dichloromethane at -10℃; for 1.5h; Stage #3: thiourea With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 2h; pH=5.5; Product distribution / selectivity; |
7-AVCA(79349-82-9) is a compound which also can be called for (6R-Trans)-7-amino-8-oxo-3-ethenyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-AMINO-3-VINYLCEPHALOSPORANIC ACID;(6R,7R)-7-Amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
Routine cases,its chemical formula is C9H10N2O3S, and can be observed as white or class white crystalline. Product Categories of 7-AVCA(79349-82-9) is Organic acids,and the structure of 7-AVCA(79349-82-9) is:
7-AVCA(79349-82-9) can be used for cefdinir Intermediate.
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