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

Base Information

• Chemical Name: 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid
• CAS No.: 84208-36-6
• Molecular Formula: C₁₈H₁₇ClN₄O₈S
• Molecular Weight: 484.874
• Mol file: 84208-36-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic 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: 82.0%

(2-chloroacetylamino-thiazol-4-yl)glyoxylic acid (73181-66-5) + O-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethyl>hydroxylamine (84208-35-5) → 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid (84208-36-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 12h; Ambient temperature; pH 5.0;

DOI:10.1248/cpb.32.2646

Reference yield:

2-chloroacetamido-4-thiazolyl acetic acid ethyl ester (19749-93-0) → 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid (84208-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 62.5 percent / SeO₂ / dioxane; acetic acid / 4 h / 110 - 115 °C

2: 84 percent / 1 N NaOH / ethanol / 1 h / Ambient temperature

3: 82 percent / 1 N NaOH / H₂O; tetrahydrofuran / 12 h / Ambient temperature; pH 5.0

With sodium hydroxide; selenium(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; acetic acid;

DOI:10.1248/cpb.32.2646

Reference yield:

4-nitrobenzyl chloride (619-73-8) → 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetic acid (84208-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 29.6 g / pyridine / diethyl ether / 5 h / Ambient temperature

2: K₂CO₃ / dimethylformamide / 24 h / Ambient temperature

3: 90 percent / hydrazine hydrate / CH₂Cl₂ / 5 h / Ambient temperature

4: 82 percent / 1 N NaOH / H₂O; tetrahydrofuran / 12 h / Ambient temperature; pH 5.0

With pyridine; sodium hydroxide; potassium carbonate; hydrazine hydrate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.2646

upstream raw materials:

(2-chloroacetylamino-thiazol-4-yl)glyoxylic acid

O-<1-methyl-1-(4-nitrobenzyloxycarbonyl)ethyl>hydroxylamine

2-chloroacetamido-4-thiazolyl acetic acid ethyl ester

4-nitrobenzyl chloride

Downstream raw materials:

2-((S)-4-{2-[2-(2-Chloro-acetylamino)-thiazol-4-yl]-2-[(Z)-1-methyl-1-(4-nitro-benzyloxycarbonyl)-ethoxyimino]-acetylamino}-3-oxo-isoxazolidin-2-yl)-5-oxo-tetrahydro-furan-2-carboxylic acid benzhydryl ester

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

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

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