(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

Chemical Name:(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS No.:208512-83-8
Molecular Formula:C₁₉H₁₅Cl₃N₂O₆S₂
Molecular Weight:537.829
Hs Code.:

(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Synonyms:(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Chemical Property of (6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Technology Process of (6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 10 articles about (6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-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: 78.0%

: 208512-82-7
(6R,7R)-7-{2-[4-((E)-2-tert-Butoxycarbonyl-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 208512-83-8
(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; methoxybenzene; for 4h;
DOI:10.1016/S0968-0896(02)00336-X

Reference yield:

: 583-78-8
2,5-dichlorophenol

: 208512-83-8
(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / I₂; AgSO₄ / CH₂Cl₂ / 24 h

2: DABCO / dimethylformamide / 1 h / 20 °C

3: 13.0 g / 2 h / 220 °C

4: 81 percent / aq. KOH / ethanol / 3 h / Heating

5: 90 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

6: 50 percent / Pd(OAc)3; PPh₃; Bu₃N / dimethylformamide / 4 h / 80 °C

7: 92 percent / aq. NaOH / 1.5 h / 20 °C

8: 54 percent / DCC / tetrahydrofuran; CH₂Cl₂ / 1.5 h

9: 78 percent / TFA / CH₂Cl₂; methoxybenzene / 4 h

With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; sodium hydroxide; silver(II) sulfate; palladium(III) acetate; tributyl-amine; iodine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; methoxybenzene; N,N-dimethyl-formamide; 3: Newman-Kwart rearrangement / 6: Heck reaction;
DOI:10.1016/S0968-0896(02)00336-X

Reference yield:

: 7587-15-7
2,3-dichloro-4-iodophenol

: 208512-83-8
(6R,7R)-7-{2-[4-((E)-2-Carboxy-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: DABCO / dimethylformamide / 1 h / 20 °C

2: 13.0 g / 2 h / 220 °C

3: 81 percent / aq. KOH / ethanol / 3 h / Heating

4: 90 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

5: 50 percent / Pd(OAc)3; PPh₃; Bu₃N / dimethylformamide / 4 h / 80 °C

6: 92 percent / aq. NaOH / 1.5 h / 20 °C

7: 54 percent / DCC / tetrahydrofuran; CH₂Cl₂ / 1.5 h

8: 78 percent / TFA / CH₂Cl₂; methoxybenzene / 4 h

With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; sodium hydroxide; palladium(III) acetate; tributyl-amine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; methoxybenzene; N,N-dimethyl-formamide; 2: Newman-Kwart rearrangement / 5: Heck reaction;
DOI:10.1016/S0968-0896(02)00336-X