sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate

Base Information

• Chemical Name: sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate
• CAS No.: 84164-44-3
• Molecular Formula: C₂₃H₂₂ClN₆O₁₃S₂*Na
• Molecular Weight: 713.035
• Mol file: 84164-44-3.mol

Synonyms:

Chemical Property of sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate

There total 32 articles about sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate 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: 77.0%

cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone (84208-38-8,84276-10-8) → sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate (84164-44-3,84518-02-5)

Guidance literature:

With sulfur trioxide; In N,N-dimethyl-formamide; at 5 ℃; for 24h;

DOI:10.1248/cpb.32.2646

Reference yield: 60.0%

trans-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone (84208-38-8,84276-10-8) → sodium trans-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate (84164-44-3,84518-02-5)

Guidance literature:

With sulfur trioxide; In N,N-dimethyl-formamide; at 5 ℃; for 24h;

DOI:10.1248/cpb.32.2646

Reference yield:

cis-3-amino-1-(2,4-dimethoxybenzyl)-4-methoxycarbonyl-2-azetidinone (61964-78-1,84187-43-9,88792-16-9,88792-17-0,88852-05-5,97591-35-0) → sodium cis-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate (84164-44-3,84518-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1: propylene oxide / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 79 percent / <1.6 molar equiv. K₂S₂O₈, K₂HPO₄ / acetonitrile; H₂O / 2 h / Heating

3: 92 percent / hydrogen / 5percent Pd-C / ethanol / 1 h / Ambient temperature

4: 77 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

5: 77 percent / 1.69 M SO₃*DMF / dimethylformamide / 24 h / 5 °C

With dipotassium hydrogenphosphate; dipotassium peroxodisulfate; sulfur trioxide; hydrogen; sodium hydrogencarbonate; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.32.2646

upstream raw materials:

trans-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone

2-chloroacetamido-4-thiazolyl acetic acid ethyl ester

4-nitrobenzyl chloride

2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid

Downstream raw materials:

sodium cis-3-<2-(2-aminothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate

sodium trans-3-<2-(2-aminothiazol-4-yl)-(Z)-2-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethoxyimino>acetamido>-4-methoxycarbonyl-2-azetidinone-1-sulfonate

Refernces