Production Method 1

1416129-92-4

898543-06-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ;  0 - 5 °C; 3 h, 0 - 5 °C

Reference

Improvement of synthesis of rivaroxaban

Fu, Jian; Zhu, Xiao-hua; Li, Qiang; Chen, Guo-hua, Anhui Yiyao, 2013, 17(6), 917-918

Production Method 2

1327778-39-1

952680-39-6

898543-06-1

1855920-51-2

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Dichloromethane ;  5 - 10 °C; 30 min, rt
1.2 30 min, rt; 12 h, rt → reflux; reflux → rt
1.3 Reagents: Hydrochloric acid Solvents: Ethanol ,  Water ;  1.5 h, pH 1 - 2, rt

Reference

An improved synthesis of (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide

Prasangi, Sridhar; Desireddy, Srinivas Reddy; Rao, Velivela Srinivsasa; Murthy, Y. L. N.; Palla, Mahesh, Chemical Science Transactions, 2017, 6(1), 27-34

4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride Raw materials

• tert-butyl {(5S)-3-[4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methylcarbamate
• Ethyl (4-(3-oxomorpholino)phenyl)carbamate
• (S,E)-1-Chloro-3-(4-chlorobenzylideneamino)propan-2-ol

4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride Preparation Products

• 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride (898543-06-1)
• N,N'-Bis4-(3-oxo-4-morpholinyl)phenylurea (1855920-51-2)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxazinanes Phenylmorpholines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxazinanes Morpholines Phenylmorpholines

Recent Advances in the Study of 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride (CAS: 898543-06-1)

The compound 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride (CAS: 898543-06-1) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This molecule, characterized by its unique oxazolidinone and morpholinone structural motifs, has shown promising potential in various therapeutic applications, particularly in the treatment of bacterial infections and inflammatory diseases. Recent studies have focused on elucidating its mechanism of action, optimizing its synthetic pathways, and evaluating its efficacy in preclinical models.

One of the key areas of research has been the exploration of the compound's antibacterial properties. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride exhibits potent activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). The study highlighted the compound's ability to inhibit bacterial protein synthesis by binding to the 50S ribosomal subunit, a mechanism similar to that of other oxazolidinone antibiotics such as linezolid. However, the unique structural features of this compound may confer advantages in terms of reduced resistance development and improved pharmacokinetic profiles.

In addition to its antibacterial effects, recent investigations have also explored the anti-inflammatory potential of this compound. A 2024 study in the European Journal of Pharmacology reported that 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride significantly reduces the production of pro-inflammatory cytokines such as TNF-α and IL-6 in vitro and in vivo. The researchers attributed this effect to the compound's modulation of the NF-κB signaling pathway, suggesting its potential utility in treating chronic inflammatory conditions such as rheumatoid arthritis and inflammatory bowel disease.

From a synthetic chemistry perspective, efforts have been made to optimize the production of 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride. A recent publication in Organic Process Research & Development detailed a novel, scalable synthetic route that improves yield and reduces the use of hazardous reagents. This advancement is critical for facilitating the compound's transition from laboratory-scale research to potential industrial production, addressing one of the key challenges in its development.

Despite these promising findings, challenges remain in the clinical translation of 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride. Pharmacokinetic studies have revealed variable oral bioavailability, prompting ongoing research into formulation strategies to enhance absorption. Additionally, comprehensive toxicological evaluations are needed to ensure the compound's safety profile meets regulatory standards. Future research directions may include structure-activity relationship (SAR) studies to further optimize the molecule's therapeutic index and the exploration of combination therapies to maximize its clinical utility.

In conclusion, 4-4-(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinylphenyl-3-morpholinone Hydrochloride (CAS: 898543-06-1) represents a compelling candidate for further development in both antibacterial and anti-inflammatory applications. The recent advancements in understanding its biological activities and synthetic optimization underscore its potential to address unmet medical needs. Continued interdisciplinary collaboration between chemists, biologists, and clinicians will be essential to fully realize the therapeutic promise of this compound.

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