{"id":10985,"date":"2022-11-15T03:40:13","date_gmt":"2022-11-14T19:40:13","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=10985"},"modified":"2022-11-15T03:40:13","modified_gmt":"2022-11-14T19:40:13","slug":"chung-john-y-l-s-team-published-research-in-organic-process-research-development-in-2015-11-20-cas-1280210-80-1","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=10985","title":{"rendered":"Chung, John Y. L.’s team published research in Organic Process Research & Development in 2015-11-20 | CAS: 1280210-80-1"},"content":{"rendered":"

Chung, John Y. L. published the artcileEvolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes<\/i><\/b>, Name: 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate<\/a>, the main research area is omarigliptin diastereoselective enantioselective preparation manufacturing route; stereoselective reductive amination arylaminopyranone mesylpyrrolopyrazole deprotection; ruthenium catalyzed enantioselective hydrogenation cycloisomerization oxidation preparation omarigliptin.<\/p>\n

Development of a convergent synthesis of omarigliptin [MK-3102, I (R = H; Ms = MeSO2)] suitable for com. manufacture is described. I (R = H) was prepared by the diastereoselective reductive amination of a nonracemic Boc-protected amino(aryl)pyranone II with mesylated pyrrolopyrazole III\u2022PhSO3H (R1 = H) [generated in situ from its Boc-protected precursor III (R1 = Boc) due to its instability and potential genotoxicity] followed by Boc deprotection. The synthesis of II relies on three Ru-catalyzed reactions: the dynamic kinetic resolution\/hydrogenation of a rac-\u03b1-aminoketone in the presence of an areneruthenium diamine complex, cycloisomerization of the bis-homopropargylic alc. product to a dihydropyran, and ruthenium-catalyzed oxidation of a pyranol (generated by hydroboration of the dihydropyran). III (R1 = Boc) was prepared regioselectively in 30:1 regioselectivity by mesylation followed by base-promoted isomerization. The Boc deprotection of III (R1 = Boc) and its reductive amination reaction with II were telescoped by using the crystallization of I (R = Boc) to remove byproducts, allowing handling of III\u2022PhSO3H (R1 = H) to be avoided and improving the overall diastereoselectivity and efficiency of the route.<\/p>\n

Organic Process Research & Development published new progress about Cycloisomerization. 1280210-80-1 belongs to class pyrazoles-derivatives, name is 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate, and the molecular formula is C12H15N3O5S2, Name: 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate<\/a>.<\/p>\n

Referemce:
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Organic Process Research & Development published new progress about Cycloisomerization. 1280210-80-1 belongs to class pyrazoles-derivatives, name is 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate, and the molecular formula is C12H15N3O5S2, Name: 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[779,131],"tags":[778],"class_list":["post-10985","post","type-post","status-publish","format-standard","hentry","category-1280210-80-1","category-pyrazoles-derivatives","tag-m-w200-350"],"yoast_head":"\nChung, John Y. L.'s team published research in Organic Process Research & Development in 2015-11-20 | CAS: 1280210-80-1 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Chung, John Y. 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L. published the artcileEvolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes, Name: 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate, the main research area is omarigliptin diastereoselective enantioselective preparation manufacturing route; stereoselective reductive amination arylaminopyranone mesylpyrrolopyrazole deprotection; ruthenium catalyzed enantioselective hydrogenation cycloisomerization oxidation preparation omarigliptin.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985\" \/>\n<meta property=\"og:site_name\" content=\"pyrazoles-derivatives\" \/>\n<meta property=\"article:published_time\" content=\"2022-11-14T19:40:13+00:00\" \/>\n<meta name=\"author\" content=\"Jessica.F\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Jessica.F\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minute\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985\",\"url\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985\",\"name\":\"Chung, John Y. 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L. published the artcileEvolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes, Name: 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole benzenesulfonate, the main research area is omarigliptin diastereoselective enantioselective preparation manufacturing route; stereoselective reductive amination arylaminopyranone mesylpyrrolopyrazole deprotection; ruthenium catalyzed enantioselective hydrogenation cycloisomerization oxidation preparation omarigliptin.\",\"breadcrumb\":{\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.pyrazoles-derivatives.com\/?p=10985#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"\u9996\u9875\",\"item\":\"https:\/\/www.pyrazoles-derivatives.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Chung, John Y. 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