(6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 219901-30-1
• Molecular Formula: C₂₁H₂₂ClNO₉S
• Molecular Weight: 499.926
• Mol file: 219901-30-1.mol

Synonyms:(6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property of (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 12 articles about (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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: 26.0%

potassium 2-acetoxybenzoate (25817-25-8) + 3-bromomethyl-7α-chloro-1,1-dioxoceph-3-em-4-carboxylic acid tert-butyl ester (148115-16-6) → (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-30-1)

Guidance literature:

In acetonitrile; at 50 ℃; for 20h;

DOI:10.1016/S0223-5234(99)80027-0

Reference yield: 26.0%

3-bromomethyl-7α-chloro-1,1-dioxoceph-3-em-4-carboxylic acid tert-butyl ester (148115-16-6) + aspirin (50-78-2,98201-60-6) → (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-30-1)

Guidance literature:

With triethylamine; for 24h; Ambient temperature;

DOI:10.1016/S0960-894X(97)00104-2

Reference yield:

t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate (33610-06-9) → (6R,7S)-3-(2-Acetoxy-benzoyloxymethyl)-7-chloro-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (219901-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / 25percent H₂O₂ / Na₂WO₄*2H₂O / acetonitrile / 24 h / 4 - 10 °C

2: i-PrONO / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 61 percent / HCl / ethyl acetate / 0.5 h

4: 40 percent / NBS / benzene / 0.5 h / Heating; Irradiation

5: 26 percent / acetonitrile / 20 h / 50 °C

With hydrogenchloride; N-Bromosuccinimide; i-propyl nitrite; dihydrogen peroxide; sodium tungstate; In dichloromethane; ethyl acetate; acetonitrile; benzene;

DOI:10.1016/S0223-5234(99)80027-0

upstream raw materials:

3-bromomethyl-7α-chloro-1,1-dioxoceph-3-em-4-carboxylic acid tert-butyl ester

aspirin

potassium 2-acetoxybenzoate

t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate

Downstream raw materials:

aspirin