(R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 162253-04-5
• Molecular Formula: C₂₄H₁₉Cl₂NO₇S
• Molecular Weight: 536.389

Synonyms:(R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 7 articles about (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 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: 81.0%

(R)-3-Acetoxymethyl-7-dichloromethylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (162252-94-0) → (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (162253-04-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.666667h; Ambient temperature; pH = 6.4 buffer;

DOI:10.1021/jm00006a022

Reference yield:

diazodiphenylmethane (908093-98-1) → (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (162253-04-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 41 percent / methanol; CH₂Cl₂ / 44 h / Ambient temperature

2: 1.) Tf₂O, Et₃N, 2.) aq. HCl / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

3: 1.) PPh₃, 2.) Zn-Cu / 1.) CH₃CN, RT, 30 min, 2.) CH₃CN, RT, 40 min

4: 81 percent / m-CPBA, buffer (pH=6.4) / CH₂Cl₂ / 0.67 h / Ambient temperature

With hydrogenchloride; trifluoromethylsulfonic anhydride; copper; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In methanol; dichloromethane;

DOI:10.1021/jm970351x

Reference yield:

benzhydryl 7-oxocephalosporanate (59128-53-9) → (R)-3-Acetoxymethyl-7-dichloromethylene-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (162253-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) PPh₃, 2.) Zn-Cu / 1.) CH₃CN, RT, 30 min, 2.) CH₃CN, RT, 40 min

2: 81 percent / m-CPBA, buffer (pH=6.4) / CH₂Cl₂ / 0.67 h / Ambient temperature

With copper; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In dichloromethane;

DOI:10.1021/jm970351x

upstream raw materials:

(R)-3-Acetoxymethyl-7-dichloromethylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

benzhydryl 7-oxocephalosporanate

benzhydryl 7-aminocephalosporanate

7-Aminocephalosporanic acid

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