Product Name

  • Name

    Cefdinir

  • EINECS 643-088-1
  • CAS No. 91832-40-5
  • Article Data31
  • CAS DataBase
  • Density 1.89 g/cm3
  • Solubility Soluble in water
  • Melting Point >180 °C dec
  • Formula C14H13N5O5S2
  • Boiling Point
  • Molecular Weight 395.42
  • Flash Point
  • Transport Information
  • Appearance Pale yellow solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 91832-40-5 (Cefdinir)
  • Hazard Symbols
  • Synonyms Cefzon;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl) (hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-, (6R-(6alpha,7beta(Z)))-;Cefdinirum [INN-Latin];(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefdinir [USAN:INN];(6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefzon (TN);Omnicef;(-)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-oxime;Omnicef (TN);Cefdinyl;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid,7-[[(2Z)-(2-amino-4- thiazolyl)(hydroxyimino)acetyl]amino]-3- ethenyl-8-oxo-,(6R,7R)-;
  • PSA 211.75000
  • LogP 0.73820

Synthetic route

7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester

7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester

1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole

1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: 7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester With N-cyclohexyl-cyclohexanamine In water; isopropyl alcohol; acetonitrile at 5 - 10℃; for 0.166667h;
Stage #2: 1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole In water; isopropyl alcohol; acetonitrile at 20℃; Further stages;		98%
potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate

potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With hydrogenchloride In water at 25 - 30℃; for 2h; pH=2.4 - 2.5;90%
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
104797-47-9

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

S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate
143183-03-3

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

cefdinir
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%
7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
128454-32-0

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With formic acid at 20℃; for 3h;2.54 g
C16H15N5O6S2
127770-93-8

C16H15N5O6S2

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With ammonium chloride; water; potassium carbonate at 18 - 22℃; pH=8 - 8.2;
7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid
128454-32-0

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

A

3-methyl cefdinir

3-methyl cefdinir

B

Cefdinir sulfoxide

Cefdinir sulfoxide

C

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-2-cephem-4-carboxylic acid

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-2-cephem-4-carboxylic acid

D

cefdinir
91832-40-5

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Conditions
ConditionsYield
With trifluoroacetic acid at 10 - 15℃; for 4h; Further byproducts.;A n/a
B n/a
C n/a
D 39.5 g
...Expand
C16H15N5O6S2*C6H15N

C16H15N5O6S2*C6H15N

A

3-methyl cefdinir

3-methyl cefdinir

B

C14H15N5O6S2

C14H15N5O6S2

C

cefdinir
91832-40-5

cefdinir

D

7β-[(E)-2-(2-amino-4-thiazolyl)-2-(hydroxyimino)acetamido]-3-vinylcephem-4-carboxylic acid

7β-[(E)-2-(2-amino-4-thiazolyl)-2-(hydroxyimino)acetamido]-3-vinylcephem-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: C16H15N5O6S2*C6H15N With ammonium chloride; potassium carbonate In tetrahydrofuran at 20 - 25℃; for 0.166667h; pH=5;
Stage #2: With sulfuric acid at 20 - 40℃; pH=2.5 - 2.6; Further stages. Title compound not separated from byproducts.;		A n/a
B n/a
C 160 g
D n/a
...Expand
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate
104797-47-9

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

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran; H2O / 6 h / 15 - 20 °C
2: ammonium chloride; potassium carbonate; water / 18 - 22 °C / pH 8 - 8.2
View Scheme
(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid

(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / triphenylphosphine; triethylamine / CH2Cl2 / 0.5 h / 10 - 30 °C
2: triethylamine / tetrahydrofuran; H2O / 6 h / 15 - 20 °C
3: ammonium chloride; potassium carbonate; water / 18 - 22 °C / pH 8 - 8.2
View Scheme
(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
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

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: PBr / tetrahydrofuran / 0.33 h / -5 °C
2.1: ethyl acetate / 5 h / 20 °C
3.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
4.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
4.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
4.3: 90 percent / H2O / -50 °C
5.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
6.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
7.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate
94796-13-1

diphenylmethyl 7β-phenylacetamido-3-vinyl-3-cephem-4-carboxylate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
1.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
1.3: 90 percent / H2O / -50 °C
2.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
3.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
4.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate
69689-86-7

ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97.6 percent / aq. NaOH / dioxane / 2 h / 100 - 110 °C
2: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
3: TFA; anisole / CH2Cl2 / 0 - 5 °C
4: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
15690-38-7

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

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: N,O-bis(trimethylsilyl)acetamide / N,N-dimethyl-acetamide / 0.5 h / 20 °C
1.2: 51.9 percent / N,N-dimethyl-acetamide / 1.5 h / -20 - -10 °C
2.1: ethyl acetate / 1 h / 20 °C
3.1: PBr / tetrahydrofuran / 0.33 h / -5 °C
4.1: ethyl acetate / 5 h / 20 °C
5.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
6.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
6.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
6.3: 90 percent / H2O / -50 °C
7.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
8.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
9.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: ethyl acetate / 1 h / 20 °C
2.1: PBr / tetrahydrofuran / 0.33 h / -5 °C
3.1: ethyl acetate / 5 h / 20 °C
4.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
5.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
5.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
5.3: 90 percent / H2O / -50 °C
6.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
7.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
8.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
28240-15-5

3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: ethyl acetate / 1 h / 20 °C
2.1: PBr / tetrahydrofuran / 0.33 h / -5 °C
3.1: ethyl acetate / 5 h / 20 °C
4.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
5.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
5.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
5.3: 90 percent / H2O / -50 °C
6.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
7.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
8.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
Diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride

Diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
2: TFA; anisole / CH2Cl2 / 0 - 5 °C
3: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate
64485-82-1

(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 52.2 percent / TEA / CHCl3 / 1.5 h / 20 °C
2: 97.6 percent / aq. NaOH / dioxane / 2 h / 100 - 110 °C
3: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
4: TFA; anisole / CH2Cl2 / 0 - 5 °C
5: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
(6R,7R)-3-Bromomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
64276-70-6

(6R,7R)-3-Bromomethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: ethyl acetate / 5 h / 20 °C
2.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
3.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
3.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
3.3: 90 percent / H2O / -50 °C
4.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
5.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
6.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate

sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
2: TFA; anisole / CH2Cl2 / 0 - 5 °C
3: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate
123201-39-8

diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino]-3-vinyl-3-cephem-4-carboxylate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TFA; anisole / CH2Cl2 / 0 - 5 °C
2: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
((6R,7R)-2-Benzhydryloxycarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl)-triphenyl-phosphonium; bromide

((6R,7R)-2-Benzhydryloxycarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl)-triphenyl-phosphonium; bromide

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 4.04 g / aq. Na2CO3 / CH2Cl2 / 1.5 h / 20 °C
2.1: PCl5; pyridine / CH2Cl2 / 1.5 h / 8 - 10 °C
2.2: MeOH / CH2Cl2 / 1.25 h / -20 - -10 °C
2.3: 90 percent / H2O / -50 °C
3.1: 92.4 percent / N,N-dimethylaniline; POCl3 / CH2Cl2 / 1.5 h / -15 - -10 °C
4.1: TFA; anisole / CH2Cl2 / 0 - 5 °C
5.1: 2.54 g / aq. HCOOH / 3 h / 20 °C
View Scheme
2-(Z)-(2-aminothiazol-4-yl)-2-hydroxyiminoacetic acid chloride/hydrochloride

2-(Z)-(2-aminothiazol-4-yl)-2-hydroxyiminoacetic acid chloride/hydrochloride

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

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 3.5h;
potassium 7-(Z)-[2-(2-aminothiazol-4-yl)-2-hydroxylminoacetimido]-3-vinyl-3-cephem-4-carboxylate
91832-41-6

potassium 7-(Z)-[2-(2-aminothiazol-4-yl)-2-hydroxylminoacetimido]-3-vinyl-3-cephem-4-carboxylate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With hydrogenchloride In water at 3 - 4℃; for 5 - 6h; pH=2.4 - 2.6; Purification / work up;
With hydrogenchloride In methanol; water at 0 - 14℃; for 5 - 6h; pH=2.2 - 2.3; Product distribution / selectivity;
With ethylenediaminetetraacetic acid In water at 25 - 30℃; for 0.25 - 0.5h; pH=1.8 - 2.4; Product distribution / selectivity; Active carbon;
With ethylenediaminetetraacetic acid In water at 8 - 30℃; for 0.25 - 0.5h; pH=1.8 - 2.4; Product distribution / selectivity; Active carbon;
N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid
865411-26-3

N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid With hydrogenchloride In water; acetone at 35 - 38℃; for 0.0833333 - 0.166667h; pH=1.2 - 1.8;
Stage #2: With ammonia; pyrographite In water; acetone at 35 - 38℃; for 0.5h; pH=6.0;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
Stage #1: N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid With hydrogenchloride In water; ethyl acetate at 35 - 38℃; for 0.0833333 - 0.166667h; pH=1.2 - 1.8;
Stage #2: With ammonia; pyrographite In water; ethyl acetate at 35 - 38℃; for 0.5h; pH=6.0;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
Stage #1: N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid With hydrogenchloride In water; isopropyl alcohol at 35 - 38℃; for 0.0833333 - 0.166667h; pH=1.2 - 1.8;
Stage #2: With ammonia; pyrographite In water; isopropyl alcohol at 35 - 38℃; for 0.5h; pH=6.0;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
benzhydryl 7-[2-(-aminothiazaol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate hydrobromide (syn isomer)
1056963-31-5

benzhydryl 7-[2-(-aminothiazaol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate hydrobromide (syn isomer)

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With trifluoroacetic acid In methoxybenzene at 5℃; for 1h; Product distribution / selectivity;
With boron trifluoride diethyl etherate In acetic acid; methoxybenzene at 10℃; for 0.333333h; Product distribution / selectivity;
Stage #1: benzhydryl 7-[2-(-aminothiazaol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate hydrobromide (syn isomer) With trifluoroacetic acid In methoxybenzene at 5 - 7℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate at 0℃; for 1h; pH=2.2; Product distribution / selectivity;
Stage #1: benzhydryl 7-[2-(-aminothiazaol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate hydrobromide (syn isomer) With boron trifluoride diethyl etherate; acetic acid In methoxybenzene at 10℃; for 0.333333h;
Stage #2: With hydrogenchloride In water pH=2.0; Product distribution / selectivity;
With trifluoroacetic acid In methoxybenzene at 5 - 7℃; for 1h; Product distribution / selectivity;
p-methoxybenzyl (Z)-7-((2-tritylamino-thiazol-4-yl)-2-trityloxyimino-acetamido)-3-vinyl-3-cephem-4-carboxylate
146667-80-3

p-methoxybenzyl (Z)-7-((2-tritylamino-thiazol-4-yl)-2-trityloxyimino-acetamido)-3-vinyl-3-cephem-4-carboxylate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: p-methoxybenzyl (Z)-7-((2-tritylamino-thiazol-4-yl)-2-trityloxyimino-acetamido)-3-vinyl-3-cephem-4-carboxylate With trifluoroacetic acid In toluene at 5 - 20℃; for 3.5h;
Stage #2: With water In toluene at 0 - 5℃; for 0.75 - 1h;
C55H49N5O5S2Si

C55H49N5O5S2Si

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: C55H49N5O5S2Si With trifluoroacetic acid In toluene at 5 - 20℃; for 3.5h;
Stage #2: With water In toluene at 0 - 50℃; Product distribution / selectivity;
7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) monohydrate

7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) monohydrate

cefdinir
91832-40-5

cefdinir

Conditions
ConditionsYield
With water for 0.0833333h;
In methanol Purification / work up;
Stage #1: 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) monohydrate at -20℃; freezing;
Stage #2: at 20℃; under 0.01 Torr; for 158h; Product distribution / selectivity; vacuum drying;
With phosphorus pentoxide at 60℃; for 1h; Product distribution / selectivity;
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium hydrogen sulfate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium hydrogen sulfate

Conditions
ConditionsYield
Stage #1: cefdinir With sulfuric acid In methanol Cooling with ice;
Stage #2: With sodium methylate In methanol for 0.25h; Product distribution / selectivity;		99%
With sulfuric acid; sodium methylate In methanol for 0.25h; Product distribution / selectivity; Cooling with ice;99%
cefdinir
91832-40-5

cefdinir

2C14H13N5O5S2*HO4S(1-)*H2O4S*K(1+)

2C14H13N5O5S2*HO4S(1-)*H2O4S*K(1+)

Conditions
ConditionsYield
With sulfuric acid; potassium propylate In ethanol for 0.25h; Product distribution / selectivity;98.3%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium dihydrogen phosphate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium dihydrogen phosphate

Conditions
ConditionsYield
Stage #1: cefdinir With phosphoric acid In ethanol
Stage #2: With sodium t-butanolate In ethanol for 0.25h; Product distribution / selectivity;		98.1%
With phosphoric acid; sodium t-butanolate In ethanol for 0.25h; Product distribution / selectivity;98.1%
cefdinir
91832-40-5

cefdinir

2C14H13N5O5S2*HO4S(1-)*H2O4S*Na(1+)

2C14H13N5O5S2*HO4S(1-)*H2O4S*Na(1+)

Conditions
ConditionsYield
With sulfuric acid; sodium methylate In ethanol for 0.25h; Product distribution / selectivity; Cooling with ice;98.1%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid potassium hydrogen sulfate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid potassium hydrogen sulfate

Conditions
ConditionsYield
Stage #1: cefdinir With sulfuric acid In methanol Cooling with ice;
Stage #2: With potassium methanolate In methanol for 0.25h; Product distribution / selectivity;		98%
With sulfuric acid; sodium methylate In metahanol for 0.25h; Product distribution / selectivity; Cooling with ice;98%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid ammonium hydrogen sulfate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid ammonium hydrogen sulfate

Conditions
ConditionsYield
With ammonium bisulphate In methanol Product distribution / selectivity;98%
With ammonium bisulphate In methanol Product distribution / selectivity;98%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino) 8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid potassium dihydrogen phosphate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino) 8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid potassium dihydrogen phosphate

Conditions
ConditionsYield
Stage #1: cefdinir With phosphoric acid In methanol
Stage #2: With potassium isopropoxide In methanol for 0.25h; Product distribution / selectivity;		97.5%
With phosphoric acid; potassium isopropoxide In methanol for 0.25h; Product distribution / selectivity;97.5%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid cesium hydrogen sulfate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid cesium hydrogen sulfate

Conditions
ConditionsYield
Stage #1: cefdinir With sulfuric acid In acetone
Stage #2: With cesium butoxide In acetone for 0.25h; Product distribution / selectivity;		97.3%
With sulfuric acid; cesium butoxide In acetone for 0.25h; Product distribution / selectivity;97.3%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo (4.2.0)oct-2-ene-2-carboxylic acid cesium dihydrogen phosphate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo (4.2.0)oct-2-ene-2-carboxylic acid cesium dihydrogen phosphate

Conditions
ConditionsYield
Stage #1: cefdinir With phosphoric acid In ethanol
Stage #2: With cesium butoxide In ethanol for 0.25h; Product distribution / selectivity;		96.8%
With phosphoric acid; cesium butoxide In ethanol for 0.25h; Product distribution / selectivity;96.8%
cefdinir
91832-40-5

cefdinir

2C14H13N5O5S2*2H2O4S*H3N

2C14H13N5O5S2*2H2O4S*H3N

Conditions
ConditionsYield
With sulfuric acid; ammonia In ethanol for 0.25h; Product distribution / selectivity; Cooling with ice;96.7%
cefdinir
91832-40-5

cefdinir

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid ammonium dihydrogen phosphate

(-)-(6R,7R)-7-((Z)-2-(2-aminothiazole-4-yl)-2-hydroxyimino-acetylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid ammonium dihydrogen phosphate

Conditions
ConditionsYield
With ammonium dihydrogen phosphate In ethanol Product distribution / selectivity;96.4%
With ammonium dihydrogen phosphate In ethanol Product distribution / selectivity;96.4%
cefdinir
91832-40-5

cefdinir

potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate

potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate

Conditions
ConditionsYield
With water; potassium acetate In acetone at 10 - 30℃; for 5h; Product distribution / selectivity;94.5%
cefdinir
91832-40-5

cefdinir

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C14H13N5O5S2*C42H70O35
1372167-37-7

C14H13N5O5S2*C42H70O35

Conditions
ConditionsYield
at 60℃; for 0.025h; Microwave irradiation; Alcohol solution;72.9%
cefdinir
91832-40-5

cefdinir

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-2-cephem-4-carboxylic acid

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-2-cephem-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: cefdinir With N-Trimethylsilylacetamide In dichloromethane for 0.5h;
Stage #2: With triethylamine In dichloromethane at 25 - 30℃; for 24h;
Stage #3: With sulfuric acid at 2 - 5℃; for 2h; pH=3.0; Further stages.;		48%
cefdinir
91832-40-5

cefdinir

cefdinir lactone

cefdinir lactone

Conditions
ConditionsYield
With trifluoroacetic acid In water at 35 - 40℃; for 1h;1%

Cefdinir Chemical Properties

Molecular Structure of Cefdinir (CAS NO.91832-40-5):

IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula: C14H13N5O5S2
Molecular Weight: 395.413520 g/mol
H bond acceptors: 10
H bond donors: 5
Freely Rotating Bonds: 6
Polar Surface Area: 158.18 Å2
Index of Refraction: 1.861
Molar Refractivity: 94.14 cm3
Molar Volume: 208.6 cm3
Surface Tension: 94.6 dyne/cm
Density: 1.89 g/cm3
Appearance: White to Light yellow  crystalline powder, odorless or slightly smelly
Melting Point: >180°C dec
Insolubility: ethanol, ether,water
Storage temp: Room temp
Categories of cefdinir (CAS NO.91832-40-5): Miscellaneous Biochemicals; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds
InChI
InChI=1/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
Smiles
N12[C@@H]([C@@H](NC(\C(c3csc(n3)N)=N/O)=O)C2=O)SCC(=C1C(O)=O)C=C

Cefdinir History

 Cefdinir (CAS NO.91832-40-5) is approved by the U.S. Food and Drug Administration in December 1997.

Cefdinir Uses

 Cefdinir (CAS NO.91832-40-5) is  a semi-synthetic broad-spectrum antibiotic used for infectious impetigo, erysipelas, subcutaneous abscesses, mastitis, trauma and post-operative superficial infection, pharyngitis, acute bronchitis, pneumonia, tonsillitis, gonococcal urethritis, intrauterine infection.

Cefdinir Toxicity Data With Reference

1.    

orl-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
2.    

ipr-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
3.    

scu-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
4.    

ivn-rat LD50:>2 g/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
5.    

orl-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
6.    

ipr-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
7.    

scu-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
8.    

ivn-mus LD50:>2 g/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
9.    

orl-dog LD50:>1 g/kg

     NIIRDN    Drugs in Japan. Ethical Drugs, 6th Edition 1982 . Edited by Japan Pharmaceutical Information Center. (Yakugyo Jiho Co., Ltd.,Tokyo, Japan.: )1995,667.

Cefdinir Safety Profile

 Moderately toxic by ingestion and intravenous routes. Low toxicity by intraperitoneal and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx and SOx.

Cefdinir Specification

 Cefdinir , with CAS number of 91832-40-5, can be called (-)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-
vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-oxime ; Cefdinirum . It is a pale yellow solid.

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