• Name

  Cefetamet hydrochloride

• EINECS 675-838-9
• CAS No. 65052-63-3
• Article Data16
• CAS DataBase
• Density 1.83 g/cm³
• Solubility
• Melting Point
• Formula C₁₄H₁₅N₅O₅S₂
• Boiling Point
• Molecular Weight 397.436
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes R36/37/38; R20/21/22
• Molecular Structure
• Hazard Symbols Xi,Xn
• 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;
• 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

Conditions	Yield
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

Conditions	Yield
With triethanolamine In water	92%

...Expand

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

Conditions	Yield
(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

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

...Expand

64485-88-7

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

65052-63-3

cefetamet

Conditions

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

65872-39-1

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

65052-63-3

cefetamet

Conditions

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

64485-89-8

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

65052-63-3

cefetamet

Conditions

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

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

Conditions	Yield
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

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water

...Expand

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

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;

...Expand

53064-79-2

iodomethyl pivaloate

65052-63-3

cefetamet

(6R,7R)-3-methyl-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)-acetamido]-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid pivaloyloxymethyl ester hydrochloride

Conditions

Conditions	Yield
Stage #1: cefetamet With tetrapropylammonium iodide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Stage #2: iodomethyl pivaloate With pyridine In 1-methyl-pyrrolidin-2-one at -10 - 20℃; for 1h; Stage #3: With hydrogenchloride In water Concentration;	94.86%

Cefetamet hydrochloride Chemical Properties