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7-AVCA
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Name

7-AVCA

 EINECS 1592732-453-0
CAS No. 79349-82-9 Density 1.55 g/cm3
PSA 108.93000 LogP 0.39170
Solubility N/A Melting Point 215-220oC
Formula C9H10N2O3S Boiling Point 540.7 °C at 760 mmHg
Molecular Weight 226.256 Flash Point 280.8 °C
Transport Information N/A Appearance White or yellowish crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 79349-82-9 (7-AVCA) Hazard Symbols N/A
Synonyms

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-ethenyl-8-oxo-, (6R-trans)-;(6R,7R)-7-Amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;7-Amino-3-vinyl-3-cephem-4-carboxylic acid;

Article Data 6

7-AVCA Synthetic route

C8H8N2O4S

1779-49-3

Methyltriphenylphosphonium bromide

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25℃; for 1.5h; pH=7 - 9; Temperature; Reagent/catalyst; Solvent;96.1%
33748-00-4

7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
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;
119608-90-1

7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
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
64308-63-0

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

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
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
104146-10-3

(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

79349-82-9

(6R,7R)-7-amino-3-vinyl-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 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

C5H3N3O2S

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefdinir

Conditions
ConditionsYield
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%

C16H14N4O4S3

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefixime

Conditions
ConditionsYield
With sodium hydrogensulfite; triethylamine In tetrahydrofuran; water at 10 - 15℃; for 5h;96.1%
79349-82-9

(6R,7R)-7-amino-3-vinyl-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

1026528-98-2

(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
ConditionsYield
With pyridine; trichlorophosphate Substitution;96%
104797-47-9

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate

79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

91832-40-5

cefdinir

Conditions
ConditionsYield
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;
79349-82-9

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

143183-03-3

S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate

91832-40-5

cefdinir

Conditions
ConditionsYield
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%

7-AVCA Chemical Properties

 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 Uses

7-AVCA(79349-82-9) can be used for cefdinir Intermediate.

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