(2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Base Information

• Chemical Name: (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• CAS No.: 177703-38-7
• Molecular Formula: C₁₅H₁₄N₂O₅S
• Molecular Weight: 334.353
• Mol file: 177703-38-7.mol

Synonyms:

Chemical Property of (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

There total 13 articles about (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-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:

(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester (380412-97-5) → (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid (177703-38-7)

Guidance literature:

With potassium hydroxide; In water; acetonitrile; at -5 ℃; for 1.5h;

DOI:10.1139/v01-100

Reference yield:

(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester (380412-97-5) → (6R,7R)-7-(phenoxyacetamido)ceph-3-em-4-carboxylic acid (36923-27-0) + (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid (177703-38-7)

Guidance literature:

With potassium hydroxide; In pyridine; at -8 ℃; for 2.5h; Title compound not separated from byproducts;

DOI:10.1139/v01-100

Reference yield:

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7) → (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid (177703-38-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 87 percent / trimethyl phosphite; magnesium sulfate / benzene / Heating

2.1: 62 percent / triethylamine / CH₂Cl₂ / 3 h

3.1: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

4.1: 50 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

5.1: 94 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

6.1: ozone / CH₂Cl₂; methanol / -78 °C

6.2: 100 percent / dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

7.1: 8.0 g / aqueous perchloric acid / CH₂Cl₂; acetone / 1.5 h

8.1: sulfuric acid / acetic acid / 2.5 h

9.1: 489 mg / p-toluenesulfonic acid monohydrate / toluene / Heating

10.1: aqueous potassium hydroxide / pyridine / 2.5 h / -8 °C

With potassium hydroxide; potassium permanganate; perchloric acid; sulfuric acid; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; toluene-4-sulfonic acid; ozone; triethylamine; phosphorous acid trimethyl ester; In pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1139/v01-100

upstream raw materials:

(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide