(Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid

Base Information

• Chemical Name: (Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid
• CAS No.: 128438-01-7
• Molecular Formula: C24H19N3O3S
• Molecular Weight: 429.499
• Hs Code.: 2934100090
• Mol file: 128438-01-7.mol

Synonyms:4-Thiazoleaceticacid, 2-amino-a-[(triphenylmethoxy)imino]-,(Z)-;(Z)-2-(2-Aminothiazol-4-yl)-2-(trityloxy)iminoacetic acid;2-(2-Amino-4-thiazolyl)-2-[(Z)-(trityloxy)imino]acetic acid;

Chemical Property of (Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 179-182 °C
• Refractive Index: 1.66
• Boiling Point: 651.477 °C at 760 mmHg
• PKA: 2.66±0.10(Predicted)
• Flash Point: 347.801 °C
• PSA: 126.04000
• Density: 1.295 g/cm³
• LogP: 5.10390

Purity/Quality:

99% ^*data from raw suppliers

(Z)-2-(2-Aminothiazol-4-yl)-2-((trityloxy)imino)aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino acetic acid

There total 7 articles about (Z)-2-(2-Aminothiazole-4-yl-)-2-trityloxyimino 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: 90.3%

ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate (128438-00-6) → (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid (128438-01-7)

Guidance literature:

ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate; With water; potassium hydroxide; In ethanol; at 20 - 30 ℃; Reflux;

With acetic acid; In ethanol; water; pH=4 - 5;

Reference yield:

trityl chloride (76-83-5) + (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1) → (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid (128438-01-7)

Guidance literature:

With hydrogenchloride; potassium hydroxide; potassium tert-butylate; In tetrahydrofuran; ice-water; ethanol; di-isopropyl ether; water; ethyl acetate;

Reference yield:

(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1) → (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid (128438-01-7)

Guidance literature:

Multi-step reaction with 2 steps

1: T-BuOK / tetrahydrofuran

2: KOH / ethanol / Saponification

With potassium hydroxide; potassium tert-butylate; In tetrahydrofuran; ethanol;

DOI:10.7164/antibiotics.53.1272

upstream raw materials:

trityl chloride

(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate

ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate

triphenylmethyl alcohol

Downstream raw materials:

S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate

(Z)-(2-aminothiazol-4-yl)triphenylmethyloxyimino acetic acid diethoxythiophosphoryl ester

diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

(6R,7R)-3-[(Z)-2-(3-Methoxy-isoxazol-5-yl)-vinyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 Hecker,Glinka,Cho,Zhang,Price,Chamberland,Griffith,Lee. "Discovery of RWJ-54428 (MC-02,479), a new cephalosporin active against resistant gram-positive bacteria". . p. 1272 - 1281. Retrieved 2007/10/03.
• 2、 -. "Process for the preparation of cephem prodrug esters". . . Retrieved 2008/06/13.