Efficient selective oxidation of alcohols to aldehydes catalyzed by a morpholinone nitroxide

Dong, Zhenhua; Gao, Pengwei; Xiao, Yihong

doi:10.1080/00397911.2019.1666284

Cited by 5 publications

(3 citation statements)

References 31 publications

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“…Hydrogen peroxide with AlCl 3 or KBr/TEMPO/pTsOH was also not successful under oxidation conditions. Using 1.5 equiv of sodium hypochlorite in the presence of a catalytic amount of TEMPO, KBr and nBu 4 Br , provided a 69% conversion of substrate 5 (Table , entry 1). Gratifyingly, raising the equivalents of sodium hypochlorite to 1.8, we obtained a complete conversion of alcohol 5 , after 15 min (Table , entry 2).…”

Section: Resultsmentioning

confidence: 99%

Improved Synthesis of the Selected Serine Protease uPA Inhibitor UAMC-00050, a Lead Compound for the Treatment of Dry Eye Disease

Ceradini

Cacivkins²,

Ramos-Llorca

et al. 2022

Org. Process Res. Dev.

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The α-aminophosphonate UAMC-00050, a newly developed trypsin-like serine protease inhibitor, is a lead compound for the treatment of dry eye syndrome and ocular inflammation. The medicinal chemistry route developed at the University of Antwerp possessed several problems hampering the scale-up such as poor yields for some of the steps, hazardous reagents, and environmental footprint. Herein, we report an optimized route for the UAMC-00050, in which environmental unfriendly solvents were excluded, hazardous reagents were replaced with safer alternatives, and are more efficient in terms of atom economy. Every reaction step was optimized to reach a higher yield, and design of experiment was used to find the optimum conditions in the last step. Furthermore, all the flash chromatography purifications of intermediates were replaced with plug filtration, slurry purifications, or crystallization. The overall yield was increased from 3% in the medicinal chemistry route to 22% in the process development route.

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Section: Resultsmentioning

confidence: 99%

Improved Synthesis of the Selected Serine Protease uPA Inhibitor UAMC-00050, a Lead Compound for the Treatment of Dry Eye Disease

Ceradini

Cacivkins²,

Ramos-Llorca

et al. 2022

Org. Process Res. Dev.

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“…Diemžēl gaiss/O2 ar (bpy)CuI/TEMPO 12 un H2O2 ar AlCl3 13 vai KBr/TEMPO/pTsOH 14 nespēja nodrošināt produkta 9 iegūšanu. No otras puses, izmantojot 1,5 ekvivalentus NaClO un TEMPO, KBr un nBu4Br katalītisko daudzumu, 15,16…”

Section: Aldehīda 9 Iegūšanaunclassified

“…Unfortunately, air/O2 with (bpy)CuI/TEMPO, 12 and H2O2 with AlCl3 13 or KBr/TEMPO/pTsOH 14 failed to provide product 9. On the other hand, using 1.5 equivalents of NaClO in the presence of a catalytic amount of TEMPO, KBr, and nBu4Br, 15,16 provided a 69 % conversion of substrate 8 (Table 2, entry 1). Gratifyingly, raising the equivalents of NaClO to 1.8, we obtained a complete conversion of alcohol 8 after 15 minutes (Table 2, entry 2).…”

Section: Preparation Of Aldehydementioning

confidence: 99%

Development of Scalable Synthesis for Selected Protease uPA Inhibitors

Ceradini¹

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α-Aminophosphonate UAMC-00050 is a lead compound for the treatment of Dry Eye Disease. The Doctoral thesis discusses the optimization of a multigram synthesis of UAMC-00050. Every step has been carefully studied to improve the yield, and design of experiment (DoE) was used in the last reaction. Yttrium triflate was discovered as an efficient green catalyst for the synthesis of a key intermediate through a one-pot three-component Birum–Oleksyszyn reaction. The overall yield was increased from 3 % in the medicinal chemistry route to 22 % in the process development route. The optimized protocol was applied, with the necessary changes for the preparation of the close analogues of UAMC-00050: UAMC-0004206 and UAMC-0004207.

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g-C3N4/H3PW4Mo8O40 S-scheme photocatalyst with enhanced photocatalytic oxidation of alcohols and sulfides

Nejat

Najminejad

Fazlali

et al. 2021

Inorganic Chemistry Communications

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Efficient selective oxidation of alcohols to aldehydes catalyzed by a morpholinone nitroxide

Cited by 5 publications

References 31 publications

Improved Synthesis of the Selected Serine Protease uPA Inhibitor UAMC-00050, a Lead Compound for the Treatment of Dry Eye Disease

Improved Synthesis of the Selected Serine Protease uPA Inhibitor UAMC-00050, a Lead Compound for the Treatment of Dry Eye Disease

Development of Scalable Synthesis for Selected Protease uPA Inhibitors

g-C3N4/H3PW4Mo8O40 S-scheme photocatalyst with enhanced photocatalytic oxidation of alcohols and sulfides

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