2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester

Base Information

• Chemical Name: 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester
• CAS No.: 380413-20-7
• Molecular Formula: C₂₂H₂₀N₂O₆S
• Molecular Weight: 440.477
• Mol file: 380413-20-7.mol

Synonyms:2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester

Chemical Property of 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester

There total 7 articles about 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl 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: 75.0%

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one (35500-75-5) + 1-benzyl 3-methyl 2-bromomalonate (132873-63-3) → 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester (380413-20-7)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In methanol; N,N-dimethyl-formamide; at -55 - 20 ℃;

DOI:10.1139/v01-100

Reference yield:

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 (380412-94-2) → 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester (380413-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

2: 75 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

With potassium permanganate; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1139/v01-100

Reference yield:

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7) → 2-((1R,5R)-7-Oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester (380413-20-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / trimethyl phosphite; magnesium sulfate / benzene / Heating

2: 62 percent / triethylamine / CH₂Cl₂ / 3 h

3: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

4: 75 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

With potassium permanganate; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; triethylamine; phosphorous acid trimethyl ester; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1139/v01-100

upstream raw materials:

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

1-benzyl 3-methyl 2-bromomalonate

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

Downstream raw materials:

2-Allyl-2-((1R,5R)-7-oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-malonic acid benzyl ester methyl ester

(4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester

(2R,6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester

(2S,6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester