Scalable Preparation of the Masked Acyl Cyanide TBS-MAC.

Haley Hinton, Jack Patterson, Jared Hume, Krunal Patel, Julie Pigza

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Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

5 authors.

Haley HintonChemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

Jack PattersonChemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

Jared HumeChemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

Krunal PatelChemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.ORCID 0000-0003-1232-3264

Julie PigzaChemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.ORCID 0000-0002-1289-5679

Funding

National Science Foundation 1848257

6 · The paper itself

Abstract

This paper describes the three-step synthesis of TBS-MAC, a masked acyl cyanide (MAC) and a versatile one-carbon oxidation state three synthon. We have developed a scalable and detailed synthesis that involves: (1) acetylation of malononitrile to form the sodium enolate, (2) protonation of the enolate to form acetylmalononitrile, and (3) epoxidation of the enol, rearrangement to an unstable alcohol, and TBS-protection to form the title compound. Both the sodium enolate and acetylmalononitrile are bench-stable precursors to the intermediate hydroxymalononitrile, which can be converted to other MAC reagents beyond TBS by varying the protecting group (Ac, MOM, EE, etc.).

Indexed as

Carboxylic AcidsCyanidesAlcoholsSodiumAlcoholsCarboxylic AcidsCyanidesSodiumMACmasked acyl cyanidescalablesynthetic equivalentsynthonumpolung

Identifiers

PMID37446749

DOI10.3390/molecules28135087

PMCPMC10343380

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.