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

Base Information

• Chemical Name: (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 120709-09-3
• Molecular Formula: C10H12N2O3 S
• Molecular Weight: 240.283
• Hs Code.: 2941905990
• Mol file: 120709-09-3.mol

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;

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

Chemical Property:

• Refractive Index: 1.685
• Boiling Point: 539.275 °C at 760 mmHg
• PKA: 2.84±0.50(Predicted)
• Flash Point: 279.944 °C
• PSA: 108.93000
• Density: 1.5 g/cm³
• LogP: 0.78180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

7APCA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7 APCA is a β-lactam compound, which are synthetic intermediates of therapeutically useful β-lactam antibiotics.

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

There total 1 articles about (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.24%

acetaldehyde (75-07-0,9002-91-9) + 7-Aminocephalosporanic acid (957-68-6) → (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid (120709-09-3)

Guidance literature:

7-Aminocephalosporanic acid; With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; In benzene; for 2h; Inert atmosphere; Reflux;

With trimethylsilyl iodide; In benzene; at 0 ℃; for 1h;

acetaldehyde; Reagent/catalyst; Further stages;

Reference yield: 97.74%

(7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid (120709-09-3) + D-2-p-hydroxyphenylglycine methyl ester (37763-23-8) → 7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid (92665-29-7)

Guidance literature:

(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;

D-2-p-hydroxyphenylglycine methyl ester; With sodium lauryl sulfate; In 1,4-dioxane; at 30 - 35 ℃; for 2h; Reagent/catalyst;

Reference yield:

(7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid (120709-09-3) + ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride → cefprozil (121412-77-9) + E-cefprozil (92676-86-3)

Guidance literature:

(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;

With hydrogenchloride; In dichloromethane; water; for 1h;

With sodium hydroxide; In dichloromethane; water; at 0 ℃; for 2h; pH=3.2;

upstream raw materials:

acetaldehyde

7-Aminocephalosporanic acid

Downstream raw materials:

cefprozil

E-cefprozil

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

Refernces