(2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
• CAS No.: 1186615-53-1
• Molecular Formula: C₂₈H₂₄Cl₂N₂O₅
• Molecular Weight: 539.415
• Mol file: 1186615-53-1.mol

Synonyms:(2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

There total 9 articles about (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-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:

(R)-3-chloromethyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester (67977-79-1) → (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester (1186615-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / NaNO₃, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr

2: 85 percent / Zn, AcOH / CH₂Cl₂ / 0 °C

3: 90 percent / BF₃*Et₂O / ethyl acetate / 25 °C

4: Cl₂ / CH₂Cl₂ / -20 °C / Irradiation

With sodium nitrate; chlorine; acetic acid; methyl p-toluene sulfonate; zinc; boron trifluoride diethyl etherate; In dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4039(01)85470-8

Reference yield:

6-epipenicillin sulfoxide (69780-18-3) → (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester (1186615-53-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / PPh₃ / toluene; CH₂Cl₂ / Heating

2: chlorine / ethyl acetate / 20 - 30 °C

3: NaHCO₃ / H₂O / 20 - 30 °C

4: 88 percent / NaNO₃, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr

5: 85 percent / Zn, AcOH / CH₂Cl₂ / 0 °C

6: 90 percent / BF₃*Et₂O / ethyl acetate / 25 °C

7: Cl₂ / CH₂Cl₂ / -20 °C / Irradiation

With sodium nitrate; chlorine; sodium hydrogencarbonate; acetic acid; methyl p-toluene sulfonate; triphenylphosphine; zinc; boron trifluoride diethyl etherate; In dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(01)85470-8

Reference yield:

epi-Secopenicillin (67977-61-1,68107-98-2) → (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester (1186615-53-1)

Guidance literature:

Multi-step reaction with 6 steps

1: chlorine / ethyl acetate / 20 - 30 °C

2: NaHCO₃ / H₂O / 20 - 30 °C

3: 88 percent / NaNO₃, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr

4: 85 percent / Zn, AcOH / CH₂Cl₂ / 0 °C

5: 90 percent / BF₃*Et₂O / ethyl acetate / 25 °C

6: Cl₂ / CH₂Cl₂ / -20 °C / Irradiation

With sodium nitrate; chlorine; sodium hydrogencarbonate; acetic acid; methyl p-toluene sulfonate; zinc; boron trifluoride diethyl etherate; In dichloromethane; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4039(01)85470-8

upstream raw materials:

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

epi-Secopenicillin

(R)-3-chloromethyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester

(R)-2-((1R,5S)-7-Oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-phenylsulfanylmethyl-but-3-enoic acid benzhydryl ester

Downstream raw materials:

(6R,7R)-7-Benzoylamino-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester