Concise asymmetric synthesis of Linezolid through catalyzed Henry reaction

Piccionello, Antonio Palumbo; Pierro, Paola; Accardo, A.; Buscemi, Silvestre; Pace, Andrea

doi:10.1039/c3ra45186k

Cited by 14 publications

(13 citation statements)

References 32 publications

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“…in DCM and the presence of TEA (1.1 equiv.). The amides 29-30 were obtained with moderate yields (78 % for 29 and 58 % for 30), what are values comparable with those described for analogous ethyl-derivatives previously [12,13].…”

Section: Chart 2 the Survey Of Chiral Ligands Used For The Study Of T...supporting

confidence: 85%

“…The aldehydes 15-20 were prepared by analogical methods, which were described previously [12,13]. The starting L-menthyl (7) and (-)-bornyl chloroformate (8) were obtained according to the modified synthetic procedure [14].…”

Section: Resultsmentioning

confidence: 99%

“…Beside this, the approaches in which the asymmetric synthesis takes place are also applicable. Recently, the utilization of asymmetric Henry reaction for the preparation of two oxazolidine-type drugs -Linezolid (1) and Rivaroxaban (2)was described [12,13]. These published papers confirmed that the application of asymmetric Henry reaction represents the promising alternative route for feasible production of these compounds.…”

Section: Introductionmentioning

confidence: 87%

“…Next, the synthetic method [12,13] of the preparation of the target oxazolidine-2-one drugs 1 and 2 from new chiral intermediates was verified (Scheme 2). For this study, the bornylderivatives 24 and 26 were chosen.…”

Section: Chart 2 the Survey Of Chiral Ligands Used For The Study Of T...mentioning

confidence: 99%

“…These published papers confirmed that the application of asymmetric Henry reaction represents the promising alternative route for feasible production of these compounds. Nevertheless, these studies gave only preliminary results, because it was included only one enantioselective catalyst 3 in the case of preparation of Rivaroxaban (1) [12] and the study of the Linezolid (2) synthesis used only commercially unavailable and poor enantioselective catalysts (max ee 72%) [13].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

The asymmetric Henry reaction as synthetic tool for production of drugs Linezolid and Rivaroxaban

Vrbický¹,

Macek²,

Pochobradský³

et al. 2022

Preprint

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The human drugs – antibiotic Linezolid (1) and anticoagulant Rivaroxaban (2) – belongs among modern pharmaceutics, which contain oxazolidine-2-one moiety bearing stereogenic centre. The chirality of these drugs is fundamental attribute of their biological activity. Herein, one of the efficient asymmetric syntheses of those drugs was studied in detail. High enantioselective catalysts were tested in the key step of the synthetic procedure, i.e. asymmetric Henry reaction, under different reaction conditions, using several starting aldehydes. The corresponding nitroaldols as chiral intermediates of those drugs were obtained in high yields and enantiomeric excess up to 91% ee.

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Section: Chart 2 the Survey Of Chiral Ligands Used For The Study Of T...supporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 87%

Section: Chart 2 the Survey Of Chiral Ligands Used For The Study Of T...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The asymmetric Henry reaction as synthetic tool for production of drugs Linezolid and Rivaroxaban

Vrbický¹,

Macek²,

Pochobradský³

et al. 2022

Preprint

View full text Add to dashboard Cite

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Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Lin,

Chang,

Chiou

et al. 2024

Asian J Org Chem

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The method for converting epoxy carbamates to oxazolidinones is outlined in this study. This innovative approach combines intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, thereby facilitating rapid conversion. Significantly, this method effectively addresses challenges associated with the use of expensive reagents, harsh reaction conditions, and prolonged reaction times, presenting a more efficient alternative. Demonstrating favorable reactivity across a diverse range of aryl groups, as well as benzyl or tert‐butyl carbamates, the method consistently yields satisfactory results, with oxazolidinone formation ranging from 55% to 99% in over 24 examples. The synthesized oxazolidinones, including 5v–5x, hold substantial promise as intermediates for the synthesis of crucial synthetic molecules. Furthermore, the versatility of this method is underscored by its successful application in the formation of the 6‐membered ring 1,3‐oxazinan‐2‐one. These findings not only contribute to the advancement of synthetic methodologies but also pave the way for a streamlined synthesis of important pharmaceutical compounds.

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Synthesis of Pharmaceutically Relevant Arylamines Enabled by a Nitroreductase from Bacillus tequilensis

Russo,

Luján,

Fraaije

et al. 2024

ChemBioChem

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Arylamines are essential building blocks for the manufacture of valuable pharmaceuticals, pigments and dyes. However, their current industrial production involves the use of chemocatalytic procedures with a significant environmental impact. As a result, flavin‐dependent nitroreductases (NRs) have received increasing attention as sustainable catalysts for more ecofriendly synthesis of arylamines. In this study, we assessed a novel NR from Bacillus tequilensis, named BtNR, for the synthesis of pharmaceutically relevant arylamines, including valuable synthons used in the manufacture of blockbuster drugs such as vismodegib, sonidegib, linezolid and sildenafil. After optimizing the enzymatic reaction conditions, high conversion of nitroaromatics to arylamines (up to 97%) and good product yields (up to 56%) were achieved. Our results indicate that BtNR has a broad substrate scope, including bulky nitro benzenes, nitro pyrazoles and nitro pyridines. Hence, BtNR is an interesting biocatalyst for the synthesis of pharmaceutically relevant amine‐functionalized aromatics, providing an attractive alternative to traditional chemical synthesis methodologies.

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Concise asymmetric synthesis of Linezolid through catalyzed Henry reaction

Cited by 14 publications

References 32 publications

The asymmetric Henry reaction as synthetic tool for production of drugs Linezolid and Rivaroxaban

The asymmetric Henry reaction as synthetic tool for production of drugs Linezolid and Rivaroxaban

Rapidly Diverse Synthesis of N‐Aryl‐5‐Substituted‐2‐Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates

Synthesis of Pharmaceutically Relevant Arylamines Enabled by a Nitroreductase from Bacillus tequilensis

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