• Name

  (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• EINECS 601-733-4
• CAS No. 120709-09-3
• Density 1.5 g/cm³
• Solubility
• Melting Point
• Formula  C₁₀H₁₂N₂O₃ S
• Boiling Point 539.275 °C at 760 mmHg
• Molecular Weight 240.283
• Flash Point 279.944 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-8-oxo-3-(1-propenyl)-, (6R,7R)- (9CI);7 APCA;
• PSA 108.93000
• LogP 0.78180

Synthetic route

75-07-0

acetaldehyde

957-68-6

7-Aminocephalosporanic acid

120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 7-Aminocephalosporanic acid With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane In benzene for 2h; Inert atmosphere; Reflux; Stage #2: With trimethylsilyl iodide In benzene at 0℃; for 1h; Stage #3: acetaldehyde Reagent/catalyst; Further stages;	84.24%

120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

37763-23-8

D-2-p-hydroxyphenylglycine methyl ester

92665-29-7

7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid With penicillin acylase at 30 - 35℃; for 0.5h; pH=7; Enzymatic reaction; Stage #2: D-2-p-hydroxyphenylglycine methyl ester With sodium lauryl sulfate In 1,4-dioxane at 30 - 35℃; for 2h; Reagent/catalyst;	97.74%

120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride

A

121412-77-9

cefprozil

B

92676-86-3

E-cefprozil

Conditions

Conditions	Yield
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid; ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride With triethylamine In dichloromethane; water at -40 - 0℃; for 3h; Stage #2: With hydrogenchloride In dichloromethane; water for 1h; Stage #3: With sodium hydroxide In dichloromethane; water at 0℃; for 2h; pH=3.2;
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid; ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride With triethylamine In ISOPROPYLAMIDE; water at -40 - 0℃; for 3h; Stage #2: With hydrogenchloride In ISOPROPYLAMIDE; water for 1h; Stage #3: With sodium hydroxide In ISOPROPYLAMIDE; water at 0℃; for 2h; pH=3.2;

...Expand

120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

A

121412-77-9

cefprozil

B

92676-86-3

E-cefprozil

Conditions

Conditions	Yield
Stage #1: potassium (R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetate With pyridine; pivaloyl chloride In DMF (N,N-dimethyl-formamide); dichloromethane at -30℃; for 2h; Stage #2: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid With triethylamine In DMF (N,N-dimethyl-formamide); dichloromethane; water at -40 - 0℃; for 3h;

120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

C12H17NO5

C22H27N3O7S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;

(6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical Properties