(5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 64370-34-9
• Molecular Formula: C₂₂H₁₉N₃O₇S
• Molecular Weight: 469.475
• Mol file: 64370-34-9.mol

Synonyms:(5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 6 articles about (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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:

[(2R)-2r-acetylsulfanyl-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (64370-33-8) → (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (64370-34-9)

Guidance literature:

In toluene; at 80 ℃; for 108h;

DOI:10.1021/ja00494a032

Reference yield:

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70850-45-2) → (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (64370-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dimethyl sulphoxide / acetic anhydride / 20 °C

2: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

3: oxalyl chloride, pyridine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With pyridine; sodium chlorite; oxalyl dichloride; dimethyl sulfoxide; recorcinol; In tetrahydrofuran; dichloromethane; water; acetic anhydride;

DOI:10.1039/c39870000081

Reference yield:

(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (111924-23-3) → (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (64370-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

2: oxalyl chloride, pyridine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With pyridine; sodium chlorite; oxalyl dichloride; recorcinol; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c39870000081

upstream raw materials:

[(2R)-2r-acetylsulfanyl-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

(2S,3R,4S,5R,6R)-3-Methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

(5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid