306274-78-2

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Oxazolidinecarboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with improved therapeutic properties.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 4-oxazolidinecarboxylic acid is utilized in the preparation of a wide range of organic compounds. Its versatility allows for the synthesis of various target molecules with potential applications in different fields.
Used in Antimicrobial Applications:
4-Oxazolidinecarboxylic acid is known for its antimicrobial properties, making it a promising candidate for the development of antibacterial and antifungal agents. Its ability to inhibit the growth of various microorganisms can be harnessed to create effective treatments for infectious diseases.
Used in Polymer Chemistry:
4-Oxazolidinecarboxylic acid has been investigated for its potential use in polymer chemistry. Its incorporation into polymer structures can lead to the development of new materials with unique properties and applications.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In asymmetric synthesis, 4-oxazolidinecarboxylic acid serves as a chiral auxiliary, helping to control the stereochemistry of the reaction and produce enantiomerically pure products. This is particularly important in the synthesis of chiral pharmaceuticals and other biologically active compounds.

Upstream product

• 50-00-0 formaldehyd 
• 56-45-1 L-serin 
• 161979-35-7 (S)-3-(tert-butoxycarbonyl)-1,3-oxazolidine-4-carboxylic acid 
• 302-84-1 serin 

Relevant academic research and scientific papers

Synthesis of (R)-2-amino-3-(xenyl-4-yl)-1-propyl alcohol

The invention relates to a preparation method of (R)-2-amino-3-(xenyl-4-yl)-1-propyl alcohol. The (R)-2-amino-3-(xenyl-4-yl)-1-propyl alcohol is prepared from a compound having a general formula (B) through ring opening reaction, wherein R1 is defined as a hydrogen atom, or a linear alkyl, or a branched alkyl, or a cyclopropyl, or a cyclobutyl, or a cyclopentyl, or a cyclohexyl, or a cycloheptyl. According to the preparation method described by the invention, the reaction condition is mild, less by-products are generated, the operation is simple and convenient, the quality of each intermediate related is controllable, and the (R)-2-amino-3-(xenyl-4-yl)-1-propyl alcohol prepared by the synthetic process has the advantages of lower cost, better product quality, fewer three wastes and a higher industrialized process degree. (The (R)-2-amino-3-(xenyl-4-yl)-1-propyl alcohol has the structural general formula shown in the specification).

Facile routes for the preparation of 3,4-disubstituted 1,3-oxazolidines and 1,2,5-trisubstituted imidazolidin-4-ones

Facile, alternative synthetic routes to (RS)-, (R)-, and (S)-3-benzyl-N-(2,6-dimethylphenyl)-1,3-oxazolidine-4-carboxamides (6), a chiral oxazolidine derivative of tocainide, are reported. The synthetic routes described herein also afforded (RS)-, (R)-, and (S)-11, which present the imidazolidin-4-one core and belong to a class of compounds interesting for their biological activities. All the final compounds and intermediates were fully characterized. Enantiomeric excesses of homochiral 6 and 11 were determined by capillary electrophoresis analysis using 2-hydroxypropyl-β-cyclodextrin or highly sulfated γ-cyclodextrin as chiral selectors.

Highly efficient small organic molecules for enantioselective direct aldol reaction in organic and aqueous media

(Chemical Equation Presented) A series of highly efficient organocatalysts have been derived from naturally available amino acids for carrying out enantioselective direct aldol reaction in both organic and aqueous medium. The aldol products were obtained in high diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee) for a broader range of substrates using 1 mol % of a catalyst. The results demonstrate that the structural features of organocatalysts play a crucial role in obtaining high optical purity of aldol adducts in an aqueous medium. Further, the role of water in increasing the rate and enantioselectivity of the reaction has been illustrated. Moreover, the aldol products have been employed in the synthesis of chiral amino alcohols which act as useful intermediates for building up complex natural products.

Synthesis of novel thiazolothiazepine based HIV-1 integrase inhibitors.

Thiazolothiazepines are among the smallest and most constrained inhibitors of human immunodeficiency virus type-1 integrase (HIV-1 IN) inhibitors (J. Med. Chem. 1999, 42, 3334). Previously, we identified two thiazolothiazepines lead IN inhibitors with antiviral activity in cell-based assays. Structural optimization of these molecules necessitated the design of easily synthesizable analogs. In order to design similar molecules with least number of substituent, herein we report the synthesis of 10 novel analogs. One of the new compounds (1) exhibited similar potency as the reference compounds, confirming that a thiazepinedione fused to a naphthalene ring system is the best combination for the molecule to accommodate into the IN active site. Thus, the replacement of sulfur in the thiazole ring with an oxygen does not seem considerably affect potency. On the other hand, the introduction of an extra methyl group at position 1 of the polycyclic system or the shift from a thiazepine to an oxazepine skeleton decreased potency. In order to understand their mode of interactions with IN active site, we docked all the compounds onto the previously reported X-ray crystal structure of IN. We observed that compounds 7-9 occupied an area close to D64 and Mg(2+) and surrounded by amino acid residues K159, K156, N155, E152, D116, H67, and T66. The oxygen atom of the oxazolo ring of 7 and 8 could chelate Mg(2+). These results indicate that the new analogs potentially interact with the highly conserved residues important for IN catalytic activities.

Zinc borohydride reduction of α-amino ketones: A highly diastereoselective synthetic route to anti-γ-hydroxy-β-amino alcohols

A highly diastereoselective synthesis of anti-γ-hydroxy β-amino alcohols via Zn(BH4)2 reductions of serine derived α-amino ketones is described. The latter were prepared from a serine derived γ-amino-β-ketosulfone via a α-alkylation-

Pseudoproline-containing analogues of morphiceptin and endomorphin-2: Evidence for a Cis Tyr-Pro amide bond in the bioactive conformation

Analogues of the opioid peptides [D-Phe3]morphiceptin (H-Tyr-Pro-D-Phe-Pro-NH2) and endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) containing the pseudoproline (ψPro) (4R)-thiazolidine-4-carboxylic acid (Cys[ψR1,R2pro])

Optically Active 4-Oxaproline Derivatives: New Useful Chiral Synthons Derived from Serine and Threonine

A very simple procedure for the preparation of chiral optically active N-protected-4-carboxy-1,3-oxazolidine (4-oxaproline) derivatives starting from serine and threonine is described which avoids the use of toxic solvents or reagents.Elaboration of these compounds allows significant improvement in the handling of serine and threonine during the multigram preparation of oligopeptide structures and affords versatile chiral building blocks for the organic synthesis.

Chiral Ligands Containing Heteroatoms:13. Optically Active 4-(2'-Pyridyl-1,3-oxazolidines: an Improved Synthesis of 2-(2'-Pyridyl)-2-aminoalcohols

An improved synthesis of 2-(2'-pyridyl)-2-aminoalcohols 1a and 1b, in enantiomerically pure form via 1,3-oxazolidine derivatives is presented.Some efficient and selective methods for both the cleavage of the oxazolidine ring and the removal of the N-Boc p

(Phosphinyloxy)acid amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-Amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline

Analogues of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and evaluated as inhibitors of angiotensin converting enzyme in vitro an in vivo. In general, the addition of lipophilic substituents to the 4-position of proline of the parent phosphate 1 resulted in substantial increases in vitro activity. The largest improvements were observed in the case of cis-benzyl (36-fold) and dithioketal (24-fold) analogues 2r and 2x, respectively. These enhancements of in vitro activity were accompanied by modest increases (2-3.5-fold) in in vivo (iv) activity. Among the various terminal amino acid replacements examined in this study, the indoline-based analogue 2i was by far the most potent compound on iv administration in the normotensive rat.