333753-67-6

Basic information

• Product Name: N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]aMino]-2-hydroxypropyl]acetaMide
• Synonyms: N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]aMino]-2-hydroxypropyl]acetaMide;(R)-N-(3-(3-fluoro-4-MorpholinophenylaMino)-2-hydroxypropyl)acetaMide;Linezolid Descarbonyl IMpurity;N,O-Descarbonyl (R)-Linezolid;Linezolid impurity B;N-[(2R)-3-(3-fluoro-4-morpholin-4-ylanilino)-2-hydroxypropyl]acetamide
• CAS NO: 333753-67-6
• Molecular Formula: C15H22FN3O3
• Molecular Weight: 311.3518832
• Product Categories: Aromatics, Chiral Reagents, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 333753-67-6.mol

Chemical Properties

• Boiling Point: 607.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.264±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.02±0.20(Predicted)
• CAS DataBase Reference: N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]aMino]-2-hydroxypropyl]acetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]aMino]-2-hydroxypropyl]acetaMide(333753-67-6)
• EPA Substance Registry System: N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]aMino]-2-hydroxypropyl]acetaMide(333753-67-6)

Safety Data

• Hazardous Substances Data: 333753-67-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide is used as an impurity in the production of Linezolid (L466500) for the purpose of ensuring the quality and safety of the final antibiotic product. The presence of this impurity is monitored and controlled during the manufacturing process to maintain the efficacy and safety profile of Linezolid.
As an impurity in the pharmaceutical industry, N-[(2R)-3-[[3-Fluoro-4-(4-Morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide plays a crucial role in the development and production of Linezolid. By understanding its chemical properties and potential effects on the final product, researchers and manufacturers can optimize the synthesis process and ensure the quality of the antibiotic medication. This impurity also serves as a valuable reference for the development of new drugs and drug delivery systems, contributing to the advancement of pharmaceutical research and innovation.

Upstream product

• 93246-53-8 3-fluoro-4-(morpholinyl)aniline 
• 75-36-5 acetyl chloride 
• 1532560-87-4 (S)-N-(3-amino-2-hydroxypropyl)-3-fluoro-4-morpholinoaniline 
• 141-78-6 ethyl acetate 
• 868405-66-7 N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline 
• 224323-47-1 (S)-N-(3-chloro-2-hydroxy-1-propyl)acetamide 
• 1532560-87-4 (R)-N-(3-amino-2-hydroxypropyl)-3-fluoro-4-morpholinoaniline 
• 108-24-7 acetic anhydride 
• 369-34-6 3,4-difluoronitrobenzene 
• 2689-39-6 3-fluoro-4-(4-morpholinyl)nitrobenzene 
• 1260086-02-9 (dl)-N-(3-chloro-2-hydroxypropyl)-3-fluoro-4-morpholinoaniline 
• 1532560-87-4 (dl)-N-(3-amino-2-hydroxypropyl)-3-fluoro-4-morpholinylaniline 

Relevant articles and documents

Seven-Step Continuous Flow Synthesis of Linezolid Without Intermediate Purification

Herein, the blockbuster antibacterial drug linezolid is synthesized from simple starting blocks by a convergent continuous flow sequence involving seven (7) chemical transformations. This is the highest total number of distinct reaction steps ever performed in continuous flow without conducting solvent exchanges or intermediate purification. Linezolid was obtained in 73 % isolated yield in a total residence time of 27 minutes, corresponding to a throughput of 816 mg h?1.

A oxazolidinone compounds of preparation method

The invention discloses a method for preparing an oxazolidinone compound. The method comprises the following steps of carrying out ammonolysis reaction on a racemic or optically active 3-chloro-2-hydroxypropyl aniline compound (2) as a starting material and ammonia in a proper solvent and under alkaline condition to obtain a 3-amino-2-hydroxypropyl aniline compound (3); carrying out acylation reaction on the compound (3) to obtain 3-acylamino-2-hydroxypropyl aniline compound (4); and carrying out cyclization reaction on the compound (4) and a corresponding acylating reagent to obtain the racemic or optically active oxazolidinone compound (II) as shown in the description, wherein R1 represents morpholinyl or 3-oxo-4-morpholinyl; R2 represents H or F; and R3 represents C1-12 alkyl, 5-chloro-thiophen-2-yl, thiophen-2-yl or 4,5-dichloro-2-yl; and the compound is a racemate and (S)- or (R)- optical isomers.

Preparing method for linezolid and intermediate thereof

The invention relates to a preparing method for linezolid and an intermediate thereof. The preparing method includes the step that 4-chloracetyl acetate compound (I) serves as a starting raw material and is subjected to asymmetric chiral reduction, acetylation, condensation, ammonolysis, Hoffman degradation, acetylation and cyclization to obtain (S)-N-[[3-[3-fluoro-4-(4-morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl] acetamide (linezolid). Compared with other linezolid synthesis methods, the preparing method is high in total yield and product purity, raw materials are cheap and easy to obtain, flammable, combustible and poisonous reagents are avoided, and the production technology is safe and environmentally friendly.

N-epoxy propyl-N-acyl aniline compounds, process for their preparation and use

The present invention discloses a class of N-epoxypropyl-N-acylaniline compounds represented by a formula (I), and further discloses a preparation method of the N-epoxypropyl-N-acylaniline compounds, and applications of the N-epoxypropyl-N-acylaniline compounds in preparation of oxazolidinone treating drugs including but being not limited to linezolid and rivaroxaban racemate or optical isomers, wherein R1 represents morpholinyl or 3-O-4-morpholinyl, R2 represents H or F, R3 represents C1-12 alkyl, thien-2-yl or 5-chlorothiophen-2-yl, and the compounds are racemates, (S)-optical isomers, or (R)-optical isomers.

A Process for preparing linezolid and its intermediate

The present invention relates to a manufacturing method of linezolid which is an oxazolidinone-based antibiotic. More specifically, the present invention relates to a novel manufacturing method of linezolid; and to an intermediate compound of linezolid, and the manufacturing method of linezolid uses a novel halomethyl ethanone compound as an intermediate for the manufacture of linezolid, thereby simplifying a manufacturing process and reducing manufacturing costs in comparison with a conventional manufacturing method. The intermediate compound is a novel compound, and is an (S)-1-(5-(halomethyl)-2, 2-dimethyl oxazolidine-3-yl)ethanone compound represented by chemical formula 1. In chemical formula 1, R is one element selected from F, Cl, Br, and I. The manufacturing method of linezolid comprises: a step (A) of performing a reaction process of a compound represented by chemical formula 1 and a compound represented by chemical formula 2 to manufacture a compound represented by chemical formula 3; a step (B) of hydrolyzing the compound represented by chemical formula 3 to obtain a compound represented by chemical formula 4; and a step (C) of performing carbonylation of the compound represented by chemical formula 4.COPYRIGHT KIPO 2016