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1 article(s) from Sagandira, Cloudius R.

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

Cloudius R. Sagandira and
Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

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Graphical Abstract

Scheme 1: Handling of azide chemistry in Tamiflu synthesis by Hayashi and co-workers [14].

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Figure 1: Synthesis of compound 2 from acyl chloride 1 via Curtius rearrangement using a continuous-flow syst...

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Scheme 2: Azide chemistry in the synthesis of Tamiflu.

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Scheme 3: Azidation of mesyl shikimate 5.

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Figure 2: Continuous-flow system for C-3 azidation of mesyl shikimate using aqueous sodium azide.

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Figure 3: Mesyl shikimate azidation conversion in a continuous-flow system using NaN₃.

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Figure 4: Desired azide 5 selectivity in a continuous-flow system using NaN₃.

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Figure 5: Effect of NaN₃ concentration on mesyl shikimate 4 conversion and azide 5 selectivity.

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Figure 6: Regio- and stereospecific nucleophilic -N₃ group attack.

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Figure 7: Continuous-flow system for C-3 azidation of mesyl shikimate using DPPA or TMSA.

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Figure 8: Mesyl shikimate azidation conversion in a continuous-flow system using DPPA.

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Figure 9: Desired azide 5 selectivity in a continuous-flow system using DPPA.

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Scheme 4: DPPA azidating mechanism in the presence of a base.

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Figure 10: Effect of TEA concentration on the reaction selectivity.

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Figure 11: Mesyl shikimate azidation conversion in a continuous-flow system using TMSA.

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Figure 12: Desired azide 5 selectivity in a continuous-flow system using TMSA.

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Figure 13: Continuous-flow system for C-3 azidation of mesyl shikimate using TBAA.

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Figure 14: Continuous-flow system for C-3 azidation of mesyl shikimate using TBAA.

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Scheme 5: C-5 azidation of acetamide 6 in our proposed route.

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Figure 15: Continuous flow system for C-5 azidation of acetamide 6 using NaN₃.

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Figure 16: Continuous-flow C-5 azidation of acetamide 6 using NaN₃.

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Figure 17: Continuous flow C-5 azidation of acetamide 6 using various azidating agents.

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Figure 18: Continuous flow synthesis of azide 7 from acetamide 6 using various azidating agents.

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Full Research Paper

Published 30 Oct 2019

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