5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-[[[[[4-[(3R)-3-ethyl-2,6-dioxo-3-piperidinyl]phenyl]amino]carb onyl]oxy]methyl]-8-oxo-, diphenylmethyl ester, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-[[[[[4-[(3R)-3-ethyl-2,6-dioxo-3-piperidinyl]phenyl]amino]carb onyl]oxy]methyl]-8-oxo-, diphenylmethyl ester, (6R,7R)-
• CAS No.: 805231-37-2
• Molecular Formula: C35H34N4O7S
• Molecular Weight: 654.744
• Mol file: 805231-37-2.mol

Synonyms:

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-[[[[[4-[(3R)-3-ethyl-2,6-dioxo-3-piperidinyl]phenyl]amino]carb onyl]oxy]methyl]-8-oxo-, diphenylmethyl ester, (6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-[[[[[4-[(3R)-3-ethyl-2,6-dioxo-3-piperidinyl]phenyl]amino]carb onyl]oxy]methyl]-8-oxo-, diphenylmethyl ester, (6R,7R)-

There total 8 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-[[[[[4-[(3R)-3-ethyl-2,6-dioxo-3-piperidinyl]phenyl]amino]carb onyl]oxy]methyl]-8-oxo-, diphenylmethyl ester, (6R,7R)- 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:

(6R,7R)-7-Allyloxycarbonylamino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (805231-43-0) → (6R,7R)-7-Amino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (805231-37-2)

Guidance literature:

With p-toluene sulfinic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane;

DOI:10.1021/jo048970i

Reference yield:

benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4) → (6R,7R)-7-Amino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (805231-37-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / pyridine; DMAP / CH₂Cl₂ / 4.5 h

2: 74 percent / trifluoroacetic acid; trifluoroacetic anhydride / CH₂Cl₂ / 0.17 h / 0 °C

3: aqueous ammonia; acetylesterase; ammonium sulfate / 2 h / 20 °C / pH 6.4 - 6.7

4: ethyl acetate

5: 78 percent / pyridine; DMAP / CH₂Cl₂ / 4.5 h

6: 73 percent / pyridine; DMAP / CH₂Cl₂ / 5 h

7: p-toluenesulfinic acid / Pd(PPh₃)4 / CH₂Cl₂

With pyridine; dmap; ammonium hydroxide; ammonium sulfate; p-toluene sulfinic acid; acetylesterase; trifluoroacetic acid; trifluoroacetic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; ethyl acetate;

DOI:10.1021/jo048970i

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-Amino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (805231-37-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / CH₂Cl₂ / 72 h / 20 °C

2: 89 percent / pyridine; DMAP / CH₂Cl₂ / 4.5 h

3: 74 percent / trifluoroacetic acid; trifluoroacetic anhydride / CH₂Cl₂ / 0.17 h / 0 °C

4: aqueous ammonia; acetylesterase; ammonium sulfate / 2 h / 20 °C / pH 6.4 - 6.7

5: ethyl acetate

6: 78 percent / pyridine; DMAP / CH₂Cl₂ / 4.5 h

7: 73 percent / pyridine; DMAP / CH₂Cl₂ / 5 h

8: p-toluenesulfinic acid / Pd(PPh₃)4 / CH₂Cl₂

With pyridine; dmap; ammonium hydroxide; ammonium sulfate; p-toluene sulfinic acid; acetylesterase; trifluoroacetic acid; trifluoroacetic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; ethyl acetate;

DOI:10.1021/jo048970i

upstream raw materials:

(6R,7R)-7-Allyloxycarbonylamino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

benzhydryl 7-aminocephalosporanate

7-Aminocephalosporanic acid

(6R,7R)-7-Allyloxycarbonylamino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid