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58909-56-1

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CAS No.: 58909-56-1
Name: (6R-trans)-7-amino-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Article Data: 8
Molecular Structure:
Molecular Structure of 58909-56-1 ((6R-trans)-7-amino-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)
Formula: C12H13 N5 O5 S2
Molecular Weight: 371.398
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-amino-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-,(6R-trans)-;7-Amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thio]methyl]cephalosporanicacid
Density: 2.03g/cm3
Boiling Point: 718℃[at 101 325 Pa]
Solubility: 200mg/L at 20℃
PSA: 202.24000
LogP: -0.80770
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Synthetic route
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2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

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7-Aminocephalosporanic acid

58909-56-1

7-aminoceftrizine

Conditions
ConditionsYield
With boron trifluoride dimethyl carbonate complex; methanesulfonic acid at 10 - 12℃; for 0.383333h; Reagent/catalyst;95.1%
With boron trifluoride dimethyl carbonate complex; edetate disodium at 30℃; for 0.833333h; Time;90%
With boron trifluoride In acetonitrile at 10 - 30℃; for 0.5h;85.71%
957-68-6

7-Aminocephalosporanic acid

1,2,3,4-Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione

58909-56-1

7-aminoceftrizine

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; acetonitrile boron trifluoride complex at 30℃; for 0.333333h;88%

(6R,7R)-7-(4-Carboxy-butyrylamino)-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

58909-56-1

7-aminoceftrizine

Conditions
ConditionsYield
With sodium hydroxide; glutaryl-7-aminocephalosporanic acid acylase In water at 25℃; pH=8.0; Enzyme kinetics; Enzymatic reaction;

C18H14N5O9PS2

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7-aminoceftrizine

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ceftriaxone

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine In ethanol; dichloromethane at 0 - 5℃; for 4h;95.7%
80756-85-0

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

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7-aminoceftrizine

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ceftriaxone disodium

Conditions
ConditionsYield
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-aminoceftrizine With triethylamine In methanol at -2 - 3℃;
Stage #2: With sodium 2-ethylhexanoic acid In water; isopropyl alcohol at 26 - 30℃; for 2h; Product distribution / selectivity;		95.5%
With sodium metabisulfite; edetate disodium; triethylamine In ethanol; water at 1 - 3℃; for 3h; Time;91%

diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate

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7-aminoceftrizine

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ceftriaxone disodium

Conditions
ConditionsYield
Stage #1: 7-aminoceftrizine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 20℃; for 2h;
Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In dichloromethane at 20℃; for 4h;
Stage #3: With sodium hydroxide In dichloromethane; water at 15 - 20℃; pH=7.5 - 7.8;		94.6%
Stage #1: 7-aminoceftrizine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 20℃; for 2h;
Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In dichloromethane at 20℃; for 18h;
Stage #1: 7-aminoceftrizine With N,O-bis-(trimethylsilyl)-acetamide In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;
Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In DMF (N,N-dimethyl-formamide) at 20℃; for 4h;
Stage #3: With sodium hydroxide In DMF (N,N-dimethyl-formamide); water at 15 - 20℃; pH=7.5 - 7.8;
Stage #1: 7-aminoceftrizine With N,N'-bis(trimethylsilyl)urea In dichloromethane at 20℃; for 2h;
Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In dichloromethane at 20℃; for 10h;
Stage #3: With sodium hydroxide In dichloromethane; water at 15 - 20℃; pH=7.5 - 7.8;

C14H24N3O5PS2

58909-56-1

7-aminoceftrizine

73384-59-5, 92143-31-2

ceftriaxone

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine In ethanol; dichloromethane at 0 - 5℃; for 4h;93.4%

C18H14N5O10PS

58909-56-1

7-aminoceftrizine

73384-59-5, 92143-31-2

ceftriaxone

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine In ethanol; dichloromethane at 0 - 5℃; for 4h;93.3%

diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate

58909-56-1

7-aminoceftrizine

73384-59-5, 92143-31-2

ceftriaxone

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine In ethanol; dichloromethane at 0 - 5℃; for 4h;92.8%
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4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate

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7-aminoceftrizine

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ceftriaxone

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine In ethanol; dichloromethane at 0 - 5℃; for 4h;91.7%
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