64485-88-7

Basic information

• Product Name: Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate
• Synonyms: ethyl 2-amino-α-(methoxyimino)-4-thiazoleacetate, predominantly syn;(Z)-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic acid ethyl ester;4-THIAZOLEACETICACID,2-AMINO-A-(METHOXYIMINO)-,ETHYLESTER,(AZ)-;EMATA(Ethyl-2-Methoxyimino-2-(2-Aminothiazol-4-yl)Acetate);ETHYL (Z)-[2-AMINO-4-THIAZOLYL] (METHOXYIMINO)ACETATECEFOTAXIME;ETHYL 2-AMINO-A-(METHOXYIMINO)-4-THIAZOLEACETATE;Ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate;2-Amino-α-[(Z)-methoxyimino]-4-thiazoleacetic acid ethyl ester
• CAS NO: 64485-88-7
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.26
• EINECS: 264-912-2
• Product Categories: Pharmaceutical Intermediates
• Mol File: 64485-88-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 162-164 °C(lit.)
• Boiling Point: 363.4 °C at 760 mmHg
• Flash Point: 173.6 °C
• Appearance: beige to yellow fine crystalline powder
• Density: 1.4042 (rough estimate)
• Vapor Pressure: 1.81E-05mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.70±0.10(Predicted)
• Water Solubility: may decompose
• CAS DataBase Reference: Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate(64485-88-7)
• EPA Substance Registry System: Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate(64485-88-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 64485-88-7(Hazardous Substances Data)

Usage

Chemical Properties

beige to yellow fine crystalline powder

Uses

Ethyl (Z)-[2-amino-4-thiazolyl](methoxyimino)acetate is used in the preparation of ceftriaxone-d3 (C245002), which is a labelled antibacterial.

InChI:InChI=1/C8H11N3O3S/c1-3-14-7(12)6(11-13-2)5-4-15-8(9)10-5/h4H,3H2,1-2H3,(H2,9,10)/b11-6+

Upstream product

• 67-56-1 methanol 
• 17356-08-0 thiourea 
• 66338-95-2 ethyl 4-chloro-2-hydroxyimino-3-oxo-butyrate 
• 141-97-9 ethyl acetoacetate 
• 77-78-1 dimethyl sulfate 
• 593-56-6 N-methoxylamine hydrochloride 
• 64987-08-2 ethyl 2-(2-aminothiazol-4-yl)glyoxylate 
• 65872-39-1 (Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester 

Downstream Products

• 117467-28-4 cefditoren pivoxil 
• 104145-95-1 cefditoren 
• 65052-63-3 cefetamet 
• 65872-41-5 cefotaxime 
• 65052-67-7 (E)-methoxyimino-(2-tritylamino-thiazol-4-yl)-acetic acid ethyl ester 
• 65052-64-4 syn-2-methoxyimino-2-(2-tritylamino-thiazol-4-yl)-acetic acid 
• 60846-21-1 cefotaxime 
• 63527-52-6 cefotaxime 
• 64485-90-1 2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid 
• 104146-53-4 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt 
• 104146-13-6 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 138450-73-4 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 138514-32-6 Pivaloyloxymethyl 7-<(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 60846-15-3 ethyl (EZ)-(2-aminothiazol-4-yl)-α-methoxyiminoacetate 

Relevant articles and documents

New cephalosporin derivatives with high antibacterial activities

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Clean preparation process of aminothiazoly loximic acid

The invention discloses a clean preparation process of aminothiazoly loximic acid, and belongs to the technical field of organic synthesis. The method comprises the following steps: (1) dropwise adding sulfuric acid into ethyl acetoacetate and calcium nitrite for oximation, separating out a calcium sulfate solid, filtering and washing wet calcium sulfate powder to obtain calcium sulfate, adding sodium carbonate into a washing solution and filtrate, and dropwise adding dimethyl sulfate for methylation of oxime; (2) after completion of the cyclization reaction, carrying out phase splitting, dehydrating an organic phase, then carrying out halogenation, adding water for quenching, carrying out phase splitting, taking strongly acidic water as a water phase and a halide as an organic phase, dropwise adding the halide into thiourea, carrying out a cyclization reaction, adding trichloromethane after completion of the cyclization reaction, and carrying out phase splitting to remove the water phase so as to obtain an ethyl aminothiazoxylate trichloromethane solution; and (3) dropwise adding liquid caustic soda, hydrolyzing, carrying out phase splitting after the reaction is finished, removing the organic phase, decolorizing the water phase, and dropwise adding the quenched water phase until the aminothiazoly loximic acid is completely separated out. The method produces less three wastes, can realize resource recycling, and is high in product yield, simple to operate and easy to realize.

Method for preparing ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate

The invention relates to a method for preparing ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate. The ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate is prepared by sequentially performing oximation reaction of a raw material ethyl acetoacetate, methylation reaction, bromination reaction and cyclization reaction in the same reactor. According to the method for preparing the ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate, each reaction step can be continuously executed in the same reactor without extraction separation treatment, and moreover, only one solvent is used for the reactions, so that purification treatment of an intermediate product and a product is greatly simplified, influence of purification operation of extraction, solvent evaporation and the like on the stability and yield of the intermediate product and the yield of the product is reduced, the yield and quality of the product are remarkably improved, the production cost is reduced, and the method is applicable to industrial production.