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3-deacetyloxy-7-aminocephalosporanic acid
ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate
cefetamet
Conditions | Yield |
---|---|
With trimethylaluminum In hexane; dichloromethane at 35℃; for 2h; Concentration; | 98.23% |
Conditions | Yield |
---|---|
With triethanolamine In water | 92% |
t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate
2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid
cefetamet
Conditions | Yield |
---|---|
(i) DCC, CH2Cl2, (ii) /BRN= 1081573/, Et3N, (iii) aq. HCO2H; Multistep reaction; |
Cefetamet pivoxil
A
(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid
B
(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
C
cefetamet
Conditions | Yield |
---|---|
With water In N,N-dimethyl-formamide at 37℃; Rate constant; phosphate buffer, var. pH; |
ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate
cefetamet
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 3 h 2: aq. NaOH / dioxane / 0.5 h / Heating 3: (i) DCC, CH2Cl2, (ii) /BRN= 1081573/, Et3N, (iii) aq. HCO2H View Scheme |
(Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester
cefetamet
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethanol; H2O / 1 h / 20 °C 2: Et3N / dimethylformamide / 3 h 3: aq. NaOH / dioxane / 0.5 h / Heating 4: (i) DCC, CH2Cl2, (ii) /BRN= 1081573/, Et3N, (iii) aq. HCO2H View Scheme |
ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate
cefetamet
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaOH / dioxane / 0.5 h / Heating 2: (i) DCC, CH2Cl2, (ii) /BRN= 1081573/, Et3N, (iii) aq. HCO2H View Scheme |
cefetamet
Conditions | Yield |
---|---|
With triethanolamine In tetrahydrofuran; water |
B
cefetamet
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water |
3-deacetyloxy-7-aminocephalosporanic acid
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
A
2-Mercaptobenzothiazole
B
cefetamet
Conditions | Yield |
---|---|
Stage #1: 3-deacetyloxy-7-aminocephalosporanic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With sodium 2-ethylhexanoate In water; acetone at 5 - 10℃; Stage #2: In water; acetone at 5℃; pH=2.5 - 3.0; |
IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Systematic of Cefetamet (CAS NO.65052-63-3): Cefetamet [USAN:INN] ; (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-methyloxime) ; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(Z)))- ; Cefetamet ; Cefetametum ; Cefetametum [Latin] ; LY097964 ; UNII-4R5TV783X3
CAS NO: 65052-63-3
Classification Code: Anti-Bacterial Agents ; Anti-Infective Agents ; Antibacterial [veterinary]
Molecular Formula of Cefetamet (CAS NO.65052-63-3): C14H15N5O5S2
Molecular Weight: 397.4294
Molecular Structure:
H bond acceptors: 10
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 158.18 Å2
Index of Refraction: 1.82
Molar Refractivity: 94.49 cm3
Molar Volume: 217 cm3
Surface Tension: 83.9 dyne/cm
Density of Cefetamet (CAS NO.65052-63-3): 1.83 g/cm3