4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester
• CAS No.: 90987-19-2
• Molecular Formula: C₂₅H₂₄ClN₃O₁₀S
• Molecular Weight: 593.999

Synonyms:4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester

Chemical Property of 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester

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Technology Process of 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester

There total 8 articles about 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl 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: 60.0%

3β-chloroacetoxy-3α-methyl-4α-(p-nitrobenzoyloxymethyl)-7β-phenoxyacetamidocepham (90987-15-8) → 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester (90987-19-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1039/P19840000413

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester (90987-19-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / pyridine / tetrahydrofuran; benzene / 15 h / 0 deg C -> room temnperature

2: 54 percent / 90percent m-chloroperbenzoic acis / CH₂Cl₂ / 1 h / 0 °C

3: 83 percent / toluene / 2 h / Heating

4: 0.055 g / AgOAc / CH₂Cl₂ / 4 h / Ambient temperature; cyclisation reaction with Br₂; cyclisation reaction of azetidinone disulphides with Br₂ in CH₂Cl₂ and CHCH₂CO₂H-AgOAC in CH₂Cl₂; interconversion reactions of penam and cepham derivatives obtained, effect of subtituents nature

5: 60 percent / 90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

With pyridine; silver(I) acetate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1039/P19840000413

Reference yield:

3α-hydroxymethyl-2,2-dimethyl-6β-phenoxyacetamidopenam (1043-94-3) → 4-Nitro-benzoic acid (2S,3S,5R,6R,7R)-3-(2-chloro-acetoxy)-3-methyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ylmethyl ester (90987-19-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / pyridine / tetrahydrofuran; benzene / 15 h / 0 deg C -> room temnperature

2: 54 percent / 90percent m-chloroperbenzoic acis / CH₂Cl₂ / 1 h / 0 °C

3: 83 percent / toluene / 2 h / Heating

4: 0.055 g / AgOAc / CH₂Cl₂ / 4 h / Ambient temperature; cyclisation reaction with Br₂; cyclisation reaction of azetidinone disulphides with Br₂ in CH₂Cl₂ and CHCH₂CO₂H-AgOAC in CH₂Cl₂; interconversion reactions of penam and cepham derivatives obtained, effect of subtituents nature

5: 60 percent / 90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

With pyridine; silver(I) acetate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1039/P19840000413

upstream raw materials:

3β-chloroacetoxy-3α-methyl-4α-(p-nitrobenzoyloxymethyl)-7β-phenoxyacetamidocepham

4-nitro-benzoyl chloride

3α-hydroxymethyl-2,2-dimethyl-6β-phenoxyacetamidopenam

O-ethyl-carbonic 6β-(2-phenoxy-acetylamino)-penicillanic anhydride

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