(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 153356-78-6
• Molecular Formula: C₃₈H₃₀N₆O₁₁S₂
• Molecular Weight: 810.822

Synonyms:

Chemical Property of (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 8 articles about (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[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:

3,4-dimethoxyphthalimide (4667-74-7) → (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (153356-78-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, 45 min

2: 49 percent / 3 h / 160 °C

3: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 3 h

4: Et₃N / dimethylsulfoxide / 1.5 h / Ambient temperature

With water; boron tribromide; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.7164/antibiotics.46.1458

Reference yield:

3,4-dimethoxyphthalic anhydride (1567-56-2) → (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (153356-78-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / NH₄OH / Heating

2: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, 45 min

3: 49 percent / 3 h / 160 °C

4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 3 h

5: Et₃N / dimethylsulfoxide / 1.5 h / Ambient temperature

With ammonium hydroxide; water; boron tribromide; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.7164/antibiotics.46.1458

Reference yield:

1,2-dimethoxy-3-methylbenzene (4463-33-6) → (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-(6,8-dioxo-2,2-diphenyl-6,8-dihydro-[1,3]dioxolo[4,5-e]isoindol-7-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (153356-78-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 70 percent / SnCl₄ / 1,2-dichloro-ethane / 1.) 0 deg C, 20 min, 2.) RT, overnight

2: 27 percent / K₂CO₃, KMnO₄ / H₂O / 1 h / 90 - 95 °C

3: 100 percent / Ac₂O / 1 h / Heating

4: 50 percent / NH₄OH / Heating

5: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, 45 min

6: 49 percent / 3 h / 160 °C

7: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 3 h

8: Et₃N / dimethylsulfoxide / 1.5 h / Ambient temperature

With ammonium hydroxide; potassium permanganate; water; acetic anhydride; boron tribromide; tin(IV) chloride; sodium hydride; potassium carbonate; triethylamine; In water; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.7164/antibiotics.46.1458

upstream raw materials:

3-(aminomethyl)-7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>ceph-3-em-4-carboxylic acid

N-carboethoxy diphenylmethylenedioxyphthalimide

3,4-dimethoxyphthalimide

3,4-dimethoxyphthalic anhydride

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