169048-79-7

Basic information

• Product Name: 2-Oxazolidinone, 5-(chloroMethyl)-, (5R)-
• Synonyms: 2-Oxazolidinone, 5-(chloroMethyl)-, (5R)-;(R)-5-ChloroMethyl-2-oxazolidinone;(R)-5-(chloromethyl)oxazolidin-2-one;(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one
• CAS NO: 169048-79-7
• Molecular Formula: C₄H₆ClNO₂
• Molecular Weight: 135.54894
• Mol File: 169048-79-7.mol

Chemical Properties

• Melting Point: 75-77 °C
• Boiling Point: 382.8±11.0 °C(Predicted)
• Appearance: /
• Density: 1.294±0.06 g/cm3(Predicted)
• PKA: 12.09±0.40(Predicted)
• CAS DataBase Reference: 2-Oxazolidinone, 5-(chloroMethyl)-, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 5-(chloroMethyl)-, (5R)-(169048-79-7)
• EPA Substance Registry System: 2-Oxazolidinone, 5-(chloroMethyl)-, (5R)-(169048-79-7)

Safety Data

• Hazardous Substances Data: 169048-79-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Oxazolidinone, 5-(chloromethyl)-, (5R)is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical properties and reactivity. Its specific stereochemistry and functional groups allow for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Oxazolidinone, 5-(chloromethyl)-, (5R)serves as a key intermediate in the synthesis of agrochemicals, contributing to the development of novel and effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
2-Oxazolidinone, 5-(chloromethyl)-, (5R)is utilized as a versatile intermediate in organic synthesis, enabling the creation of a wide range of organic compounds with diverse applications across various industries. Its unique structure and reactivity facilitate the synthesis of complex molecules and the development of innovative chemical processes.

Upstream product

• 113420-86-3 (5R)-5-(methanesulfonyloxymethyl)oxazolidin-2-one 
• 100-66-3 methoxybenzene 
• 336628-52-5 (5R,1'S)-5-chloromethyl-3-(1'-phenylethyl)-2-oxazolidinone 
• 917-61-3 sodium isocyanate 
• 106-89-8 epichlorohydrin 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 590-28-3 potassium cyanate 
• 226213-72-5 (R)-4-chloro-3-hydroxybutanamide 

Relevant articles and documents

Synthesis and biological activity evaluation of novel heterocyclic pleuromutilin derivatives

A series of pleuromutilin derivatives were synthesized by two synthetic procedures under mild reaction conditions and characterized by Nuclear Magnetic Resonance (NMR), Infrared Spectroscopy (IR), and High Resolution Mass Spectrometer (HRMS). Most of the derivatives with heterocyclic groups at the C-14 side of pleuromutilin exhibited excellent in vitro antibacterial activities against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE), and vancomycin-resistant Enterococcus (VRE) in vitro antibacterial activity. The synthesized derivatives which contained pyrimidine rings, 3a, 3b, and 3f, displayed modest antibacterial activities. Compound 3a, the most active antibacterial agent, displayed rapid bactericidal activity and affected bacterial growth in the same manner as that of tiamulin fumarate. Moreover, molecular docking studies of 3a and lefamulin provided similar information about the interactions between the compounds and 50S ribosomal subunit. The results of the study show that pyrimidine rings should be considered in the drug design of pleuromutilin derivatives.

Electrogenerated chiral 4-methoxy-2-oxazolidinones as diastereoselective amidoalkylation reagents for the synthesis of β-amino alcohol precursors

A flexible and efficient synthesis of enantiomerically pure 4,5-substituted 2-oxazolidinones - important target molecules as precursors of pharmacologically active 2-oxazolidinones, β-amino alcohols, β-blockers and azasugar derivatives - is described. As starting materials, the enantiopure storage forms of chiral N-acyliminium ions (4RS,5S)-5-chloromethyl-4-methoxy-1,3-oxazolidin-2-one (2) and (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one (3) were used; these are readily available from the chiral pool with the aid of electrochemical transformations. Substitution of the 4-methoxy group in building blocks 2 and 3 with a large variety of organometallic nucleophiles resulted in the trans-diastereoselective formation of enantiopure 4,5-disubstituted 2-oxazolidinones, with a high degree of flexibility in the substituent at the 4-position.

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

Design and synthesis of 2-amino-6-(1H,3H-benzo[de]isochromen-6-yl)-1,3,5- triazines as novel Hsp90 inhibitors

A novel series of 2-amino-1,3,5-triazines bearing a tricyclic moiety as heat shock protein 90 (Hsp90) inhibitors is described. Molecular design was performed using X-ray cocrystal structures of the lead compound CH5015765 and natural Hsp90 inhibitor geldanamycin with Hsp90. We optimized affinity to Hsp90, in vitro cell growth inhibitory activity, water solubility, and liver microsomal stability of inhibitors and identified CH5138303. This compound showed high binding affinity for N-terminal Hsp90α (Kd = 0.52 nM) and strong in vitro cell growth inhibition against human cancer cell lines (HCT116 IC50 = 0.098 μM, NCI-N87 IC50 = 0.066 μM) and also displayed high oral bioavailability in mice (F = 44.0%) and potent antitumor efficacy in a human NCI-N87 gastric cancer xenograft model (tumor growth inhibition = 136%).

A facile synthesis of the oxazolidinone antibacterial agent linezolid

A facile synthetic route of linezolid 1 has been developed. Using commercially available (R)-epichlorohydrin as the starting material, 1 was obtained through a sequence of cyclization, substitution, a Goldberg coupling, aminolysis and acetylation reactions. The synthetic route is easy to perform and can be scaled up.

Design and enantiopure synthesis of (R)-2-((2-Oxooxazolidin-5-yl)methyl) isoindoline- 1, 3-dione: A key precursor to build 2-oxazolidinone class of antibacterial agents

A new synthetic method for the preparation of high enantiopure (R)-2-((2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione has been developed. The enantiopurity of the obtained (R)-2-((2-oxooxazolidin-5-yl)methyl) isoindoline-1,3-dione is established using

2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy

The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27 mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series.

Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

(Chemical Equation Presented) Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.

CETP INHIBITORS DERIVED FROM BENZOXAZOLE ARYLAMIDES

Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones

A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from β-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral β-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (～99%) and d.e. (>99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products.