Stereoselective synthesis of erythro-β-chloroamines and their conversion into functionalized trans-oxazolidin-2-ones

Slama, Soumaya; Besbes, Rafâa

doi:10.1016/j.tet.2014.05.063

Cited by 6 publications

(5 citation statements)

References 78 publications

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“…It should be pointed out that oxazolidinones cis-2b-d were obtained as a racemic mixture of 1/1 diastereomeric product, which were derived from the 1/1 diastereomeric mixture of the starting β-amino alcohols 3b-d [72]. Diastereomeric products (cis-2b and cis-2d) were separated by silica gel column chromatography for characterization purposes and their spectroscopic characteristics were determined (see Supporting Info).…”

Section: Resultsmentioning

confidence: 99%

A Convenient Access to Functionalized Oxazol-2-One-5-Carboxylates from β-Aminoalcohols Through NBS-Light Mediated Oxidation of Cis- or Trans-N-Alkyloxazolidinones

et al. 2020

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Section: Resultsmentioning

confidence: 99%

A Convenient Access to Functionalized Oxazol-2-One-5-Carboxylates from β-Aminoalcohols Through NBS-Light Mediated Oxidation of Cis- or Trans-N-Alkyloxazolidinones

et al. 2020

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“…Preparation of oxazolidinone as an API precursor has been reported via ring expansion of N-Boc aziridines [ 111 ] and cyclization of β -chloramines [ 112 ]. Both routes used 1,2-amino alcohols as a starting material.…”

Section: Photochemistrymentioning

confidence: 99%

Continuous-Flow Chemistry and Photochemistry for Manufacturing of Active Pharmaceutical Ingredients

Horáková

Kočí

2022

Molecules

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An active pharmaceutical ingredient (API) is any substance in a pharmaceutical product that is biologically active. That means the specific molecular entity is capable of achieving a defined biological effect on the target. These ingredients need to meet very strict limits; chemical and optical purity are considered to be the most important ones. A continuous-flow synthetic methodology which utilizes a continuously flowing stream of reactive fluids can be easily combined with photochemistry, which works with the chemical effects of light. These methods can be useful tools to meet these strict limits. Both of these methods are unique and powerful tools for the preparation of natural products or active pharmaceutical ingredients and their precursors with high structural complexity under mild conditions. This review shows some main directions in the field of active pharmaceutical ingredients’ preparation using continuous-flow chemistry and photochemistry with numerous examples of industry and laboratory-scale applications.

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“…Oxazolidinone 5 (Scheme ) has recently attracted our attention as an API (active pharmaceutical ingredient) precursor. Preparation of this scaffold has been reported via ring expansion of N‐Boc aziridines and cyclization of β‐chloroamines . Both routes used 1,2‐aminoalcohols as starting material.…”

Section: Introductionmentioning

confidence: 99%

“…Preparation of this scaffold has been reported via ring expansion of N-Boc aziridines [10] and cyclization of b-chloroamines. [11] Both routes used 1,2-aminoalcohols as starting material. In 2006, Crich and Banerjee [12] described a method for the synthesis of 5 from widely available L-phenylalanine methyl ester hydrochloride (1; Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Continuous Flow Photochemical Benzylic Bromination of a Key Intermediate in the Synthesis of a 2‐Oxazolidinone

Chen

Frutos²,

Mateos³

et al. 2018

ChemPhotoChem

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A continuous flow procedure for the benzylic photobromination of methyl N,N‐bis (tert‐butoxycarbonyl) phenylalaninate is presented. This photochemical transformation generating the brominated intermediate is the critical step in the synthesis of the oxazolidinone methyl (4S,5R)‐3‐N‐tert‐Butoxycarbonyl‐5‐phenyl‐1,3‐oxazolidin‐2‐oxo‐4‐carboxylate, a key intermediate for the preparation of active pharmaceutical ingredients. The reaction was optimized in three continuous flow photoreactors: A self‐made reactor based on a T5 8 W black light lamp, as well as the commercially available VapourTec® UV‐150 and Corning® Advanced‐Flow™ reactors, both equipped with LED light sources. Under optimal conditions, concentrated solutions (95 g/L) of the starting material could be processed on a multi‐gram scale, providing high conversion (96 %) within 7 min at 30 °C, using 2 equivalents of N‐bromosuccinimide (NBS).

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Stereoselective synthesis of erythro-β-chloroamines and their conversion into functionalized trans-oxazolidin-2-ones

Cited by 6 publications

References 78 publications

A Convenient Access to Functionalized Oxazol-2-One-5-Carboxylates from β-Aminoalcohols Through NBS-Light Mediated Oxidation of Cis- or Trans-N-Alkyloxazolidinones

A Convenient Access to Functionalized Oxazol-2-One-5-Carboxylates from β-Aminoalcohols Through NBS-Light Mediated Oxidation of Cis- or Trans-N-Alkyloxazolidinones

Continuous-Flow Chemistry and Photochemistry for Manufacturing of Active Pharmaceutical Ingredients

Continuous Flow Photochemical Benzylic Bromination of a Key Intermediate in the Synthesis of a 2‐Oxazolidinone

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