64485-90-1

Basic information

• Product Name: (Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINO ACETIC ACID
• Synonyms: (Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINOACETIC ACID;TTMA:( Z )-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINOACETIC ACID;(αZ)-α-(MethoxyiMino)-2-[(triphenylMethyl)aMino]-4-thiazoleacetic Acid;2-[(Z)-MethoxyiMino]-2-[2-(tritylaMino)thiazol-4-yl]acetic Acid;(Z)-2-(2-TritylaMinothiazol-4-...
• CAS NO: 64485-90-1
• Molecular Formula: C₂₅H₂₁N₃O₃S
• Molecular Weight: 443.52
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 64485-90-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 642.4 °C at 760 mmHg
• Flash Point: 342.3 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 2.21E-17mmHg at 25°C
• Refractive Index: 1.64
• Solubility: Chloroform, DMSO, Methanol
• PKA: 2.66±0.41(Predicted)
• CAS DataBase Reference: (Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINO ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINO ACETIC ACID(64485-90-1)
• EPA Substance Registry System: (Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-METHOXYIMINO ACETIC ACID(64485-90-1)

Safety Data

• Hazardous Substances Data: 64485-90-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Cephalosporin derivatives.

InChI:InChI=1/C25H21N3O3S/c1-31-28-22(23(29)30)21-17-32-24(26-21)27-25(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3,(H,26,27)(H,29,30)/b28-22-

Upstream product

• 64485-89-8 ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate 
• 76-83-5 trityl chloride 
• 65872-41-5 cefotaxime 
• 64485-88-7 ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate 

Downstream Products

• 65052-63-3 cefetamet 
• 111540-31-9 4-styryl 3-<<(2-trityl-amino 4-thiazolyl)(methoxyimino)acetyl>amino> 2-azetidinone 
• 135587-52-9 (2R,2aR,7aS)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-1-oxo-6-phenyl-2,2a-dihydro-1H,7H-3-thia-7b-aza-cyclobuta[e]indene-7a-carboxylic acid 
• 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 
• 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 
• 104112-35-8 N-((2S,3S)-2-Fluoromethyl-4-oxo-azetidin-3-yl)-2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetamide 
• 142466-80-6 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-ethoxycarbonylmethyl-2-azetidinone 
• 142466-81-7 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-t-butyloxycarbonylmethyl-2-azetidinone 
• 141992-85-0 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-(t-butyloxycarbonylmethylcarbamoylmethyl)-2-azetidinone 
• 143677-60-5 <4-bis<2Z-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetyl>amino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl>acetate de tert-butyle 
• 76470-69-4 (6R,7S)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 76470-70-7 (4S,6R,7S)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-4-methyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 117901-29-8 amino-2 N-<(hydroxy-4 phenyl)-1 oxo-2 azetidinyl-3> (methoxyimino)-α thiazolyl-4 acetamide (3-S) (Z) 
• 117901-28-7 amino-2 N-<(hydroxy-3 phenyl)-1 oxo-2 azetidinyl-3> (methoxyimino)-α thiazolyl-4 acetamide (3-S) (Z) 

Relevant articles and documents

Preparation method of triphenylmethyl aminothiazoly loximic acid

The invention belongs to the field of preparation of organic compounds, and particularly relates to a preparation method of triphenylmethyl aminothiazoly loximic acid, which comprises the following steps: 1, dissolving aminothiazoly loximic acid and diisopropylethylamine in dichloromethane, and dropwisely adding triphenylchloromethane to react to obtain a reaction solution; 2, adding an acidic solution into the reaction solution obtained in the step 1, adjusting to be acidic, separating the solution, and reserving an organic phase; 3, dropwise adding an alkaline solution into the organic phase in the step 2, filtering, and respectively leaching with dichloromethane and water to obtain precipitates; and 4, adding water into the precipitate obtained in the step 3, pulping, dropwise adding an acidic solution into the precipitate in the pulping process, adjusting to acidity, filtering, and drying to obtain the triphenylmethyl aminothiazoly loximic acid. By using the method provided by the invention, DMF is prevented from being used as a solvent, less waste is generated, the subsequent operation steps are simple, the yield of the obtained triphenylmethyl aminothiazoly loximic acid is greater than 94%, and the purity of the obtained triphenylmethyl aminothiazoly loximic acid is higher than 99%.

Synthesis and oral activity of pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylt hiazol-5-yl)vinyl-3-cephem-4 carboxylate (ME1207) and its related compound

7-[2-(2-Aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3(Z)-(4-methylth iazol-5-yl)vinyl-3-cephem-4-carboxylic acid (11, ME1206) and its 3-trans isomer (13) were prepared to test antibacterial activity. These compounds exhibited excellent antibacterial activity against both gram-positive and gram-negative bacteria, including β-lactamase producing strains. The pivaloyloxymethyl esters (12 and 14) of the compounds (11 and 13) were prepared by esterification with pivaloyloxymethyl iodide. Among them, pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylt hiazol-5-yl)vinyl-3-cephem-4-carboxylate (12, ME1207) showed good urinary recovery after oral administration in mice.

Cephalosporins

Compounds of the formula STR1 wherein R1 is hydrogen or a conventional amino-protecting group, and R2 is a straight or branched chain alkyl group containing from 1 to 4 carbon atoms, allyl, 2-butenyl or 3-butenyl, and nontoxic pharmaceutically acceptable salts and solvates thereof, as well as processes for their preparation, are disclosed. The compounds in which R1 is hydrogen are potent antibacterial agents.