1220910-89-3

Basic information

• Product Name: CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester
• Synonyms: Torezolid Intermediate1;N- [3- fluoro-4- [6- (2-methyl--2H- tetrazol-5-yl) -3-pyridinyl] phenyl] carbamate;CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester;N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester;N-[3-Fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]carbaMic acid phenylMethyl ester;benzyl (3-fluoro-4-(6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbaMate;N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-;Benzyl {3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phe nyl}carbamate
• CAS NO: 1220910-89-3
• Molecular Formula: C₂₁H₁₇FN₆O₂
• Molecular Weight: 404.3970832
• Product Categories: Tedizolid intermediates
• Mol File: 1220910-89-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.52±0.70(Predicted)
• CAS DataBase Reference: CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester(1220910-89-3)
• EPA Substance Registry System: CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester(1220910-89-3)

Safety Data

• Hazardous Substances Data: 1220910-89-3(Hazardous Substances Data)

Usage

Uses

N-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]carbamic Acid Phenylmethyl Ester is an intermediate in the synthesis of Tedizolid (T013750), an known oral and intravenous antibiotic.

Upstream product

• 345963-96-4 (2-fluoro-4-iodophenyl)-acetic acid 
• 315228-19-4 2-(2-fluoro-4-nitrophenyl)acetic acid 
• 883231-14-9 (6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)boronic acid 
• 380380-64-3 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 
• 501-53-1 benzyl chloroformate 
• 1056039-83-8 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 
• 874290-59-2 2-fluoro-4-(benzyloxycarbonyl)aminophenylboronic acid 

Downstream Products

• 856866-72-3 (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one 
• 1835340-19-6 (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate 

Relevant articles and documents

Efficient preparation method of tedizolid intermediate and intermediate

The invention relates to the technical field of synthesis of drug intermediates, in particular to an efficient preparation method of a tedizolid intermediate and the intermediate. The preparation method comprises the following steps: 1) reacting 2-fluoro-4-substituted phenylacetic acid with a Vilsmeier reagent, and then adding a reaction solution into an MX aqueous solution for quenching to obtain an intermediate as shown in a formula (II); 2) performing a one-pot method on the intermediate as shown in the formula (II) obtained in the step 1) and 1-(2-methyl-2H-tetrazole-5-yl) ethanone in the presence of alkali and an ammonia source to obtain an intermediate as shown in the formula (I); the invention provides a novel method for efficiently preparing the tedizolid intermediate. According to the method, the pyridine ring of the key intermediate shown in the formula (I) is obtained by cyclization of 1-(2-methyl-2H-tetrazole-5-yl) ethanone and Vinamidinium salt, meanwhile, a key methyl tetrazole group is introduced into the structure; the use of highly toxic reagents such as sodium cyanide and sodium azide is successfully avoided; the use of an expensive palladium catalyst is avoided; the methylation reaction with low selectivity is avoided.

Preparation method of tedizolid phosphate and intermediate thereof

The invention discloses a preparation method of tedizolid phosphate and an intermediate thereof. The preparation method of a tedizolid phosphate intermediate II comprises the following steps: 1, in anorganic solvent, under a condition of presence of a catalyst and zinc powder, performing a reaction on 3-fluorine-4-bromophenyl amino benzyl formate so as to obtain a solution of a tedizolid phosphate intermediate III; and 2, in an organic solvent, under a condition of presence of a palladium catalyst and a base, performing a coupling reaction on the solution of the tedizolid phosphate intermediate III obtained in the step 1 with 2-methyl-5-(5-bromopyridine-2-yl) tetrazole, so as to obtain the tedizolid phosphate intermediate II. The preparation method disclosed by the invention is free of toxic reagent, mild in reaction condition, safe to operate, environmentally friendly, high in yield, high in prepared product purity and low in production cost. Tedizolid phosphate prepared from the tedizolid phosphate intermediate II disclosed by the invention is high in yield, high in purity, capable of meeting raw material medicine standards and applicable to industrial production.

New synthesis process of oxazolinone antibiotic

According to the method of the present invention, a methyl tetrazole pyridine bromide (2) and pinacol diboron are subjected to a reaction under catalysis of a transition metal to obtain a boronic acid pinacol ester (3), the compound (3) is separated or is not separated, and the separated compound (3) or the un-separated compound (3) and Cbz-protected bromobenzene (4) are subjected to a reaction under catalysis of a transition metal to obtain a key intermediate (1) of tedizolid. According to the present invention, the compound (3) is not subjected to separation purification, and reacts with the compound (4) in a kettle to generate the compound (1).