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65052-63-3

Basic Information
CAS No.: 65052-63-3
Name: Cefetamet hydrochloride
Article Data: 16
Molecular Structure:
Molecular Structure of 65052-63-3 (Cefetamet hydrochloride)
Formula: C14H15N5O5S2
Molecular Weight: 397.436
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-,[6R-[6a,7b(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-,(6R,7R)- (9CI);Altamet;Antibiotic Ro 15-8074;Cefetamet;Cepime O;Deacetoxycefotaxime;FR 13300;LY 97964;Ro 15-8074;Ro 15-8074/005;Ultipime O;
EINECS: 675-838-9
Density: 1.83 g/cm3
Hazard Symbols: Xi,Xn
Risk Codes: R36/37/38; R20/21/22
PSA: 200.75000
LogP: 0.74430
Synthetic route
22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9

3-deacetyloxy-7-aminocephalosporanic acid

64485-88-7

ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate

65052-63-3

cefetamet

Conditions
ConditionsYield
With trimethylaluminum In hexane; dichloromethane at 35℃; for 2h; Concentration;98.23%
109-99-9

tetrahydrofuran

ester, 2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino acetate

ester, 2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino acetate

7-Aminodiacetyloxy cephalosporanic acid

65052-63-3

cefetamet

Conditions
ConditionsYield
With triethanolamine In water92%
33610-06-9

t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate

64485-90-1

2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid

65052-63-3

cefetamet

Conditions
ConditionsYield
(i) DCC, CH2Cl2, (ii) /BRN= 1081573/, Et3N, (iii) aq. HCO2H; Multistep reaction;
65243-33-6

Cefetamet pivoxil

A

126747-54-4

(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

126617-54-7

(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

65052-63-3

cefetamet

Conditions
ConditionsYield
With water In N,N-dimethyl-formamide at 37℃; Rate constant; phosphate buffer, var. pH;
64485-88-7

ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate

65052-63-3

cefetamet

Conditions
ConditionsYield
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
65872-39-1

(Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester

65052-63-3

cefetamet

Conditions
ConditionsYield
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
64485-89-8

ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate

65052-63-3

cefetamet

Conditions
ConditionsYield
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
ester, 2-mercapto-5-phenyl-1,3, 4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate

ester, 2-mercapto-5-phenyl-1,3, 4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate

7-Aminodiacetyloxy cephalosporanic acid

65052-63-3

cefetamet

Conditions
ConditionsYield
With triethanolamine In tetrahydrofuran; water
7-amino-3-desacetoxycephalosporanic acid

7-amino-3-desacetoxycephalosporanic acid

2-mercapto-5-methyl-1,3,4-thiadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

A

3-Methyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid

B

65052-63-3

cefetamet

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water
22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9

3-deacetyloxy-7-aminocephalosporanic acid

80756-85-0

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

A

149-30-4

2-Mercaptobenzothiazole

B

65052-63-3

cefetamet

Conditions
ConditionsYield
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;
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Chemistry

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