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

Base Information

• Chemical Name: (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dimethyl ester
• CAS No.: 380413-00-3
• Molecular Formula: C₁₉H₂₀N₂O₈S
• Molecular Weight: 436.442

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dimethyl 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: 36.0%

(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 dimethyl ester (380412-99-7) → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dimethyl ester (380413-00-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 1h;

DOI:10.1139/v01-100

Reference yield:

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one (35500-75-5) → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dimethyl ester (380413-00-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

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

3: 68 percent / iodine / CH₂Cl₂; H₂O / 6 h / 20 °C

4: 36 percent / sodium periodate / methanol; H₂O / 2 h / 35 °C

5: 36 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h

With sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

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) → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dimethyl ester (380413-00-3)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 50 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

3: 94 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

4: 68 percent / iodine / CH₂Cl₂; H₂O / 6 h / 20 °C

5: 36 percent / sodium periodate / methanol; H₂O / 2 h / 35 °C

6: 36 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h

With potassium permanganate; sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1139/v01-100

upstream raw materials:

(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 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

Downstream raw materials:

(6R,7R)-4-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester

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

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