Ethylene Oxide

Thomas, Edward

doi:10.1002/047084289x.re078

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2023

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“…Since this reaction uses DPPA as a non-explosive azide source, it is expected to be safer to perform even on a large scale, and there is no regulatory hurdle for its storage. The driving force for the reaction is the energetically stable PO bond formation.…”

Section: Resultsmentioning

confidence: 99%

Stereoinvertive Deoxyamination of trans-2-Aminocyclohexanol Using Bose–Mitsunobu Azidation and Staudinger Reaction for the Stereoselective Synthesis of Edoxaban

Ochiai,

Kubota,

Sasagawa

et al. 2023

Org. Process Res. Dev.

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Stereoinvertive deoxyamination involving Bose−Mitsunobu azidation and the Staudinger reaction, which proceeds under mild conditions in the presence of a neighboring group, was successfully applied for the synthesis of edoxaban. The one-pot process allowed access to key intermediates of edoxaban without isolating azide intermediates. Furthermore, the efficiency of the Bose−Mitsunobu azidation was dramatically improved by changing the substituent on the neighboring group from the Boc group to a thiazole carbonyl unit.

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Section: Resultsmentioning

confidence: 99%