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Rapid and straightforward transesterification of sulfonyl carbamates
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Science for Life Laboratory, SciLifeLab. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
Uppsala University, Science for Life Laboratory, SciLifeLab. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
2016 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 57, no 13, 1476-1478 p.Article in journal (Refereed) Published
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Text
Abstract [en]

A fast and convenient method for the alkoxy exchange of sulfonyl carbamates by simply heating in a chosen alkyl alcohol is described. No catalysts or additives are required. Microwave heating at 100-120 degrees C for 20-60 min resulted in good to excellent yields (53-93%) of alkyl (arylsulfonyl)carbamates where the alkyl part originates from the alcohol solvent. The developed protocol was applied to the synthesis of an angiotensin II type 2 receptor (AT2R) ligand.

Place, publisher, year, edition, pages
2016. Vol. 57, no 13, 1476-1478 p.
Keyword [en]
Sulfonyl carbamates, O-alkyl exchange, Transesterification, Carboxylic acid bioisosteres, AT2R ligand
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-294300DOI: 10.1016/j.tetlet.2016.02.071ISI: 000372690800018OAI: oai:DiVA.org:uu-294300DiVA: diva2:929566
Funder
EU, FP7, Seventh Framework Programme, REGPOT-CT-2013-316149-InnovaBalt
Available from: 2016-05-19 Created: 2016-05-18 Last updated: 2017-04-10Bibliographically approved

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Isaksson, RebeckaLarhed, MatsWannberg, Johan
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Organic Pharmaceutical ChemistryScience for Life Laboratory, SciLifeLabDepartment of Medicinal Chemistry
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