10140-87-1Relevant articles and documents
A Continuous Flow Sulfuryl Chloride-Based Reaction - Synthesis of a Key Intermediate in a New Route toward Emtricitabine and Lamivudine
Berton, Mateo,De Souza, Juliana M.,McQuade, D. Tyler,Snead, David R.
, p. 2271 - 2280 (2020/11/23)
We demonstrate a continuous two-step sequence in which sulfenyl chloride is formed, trapped by vinyl acetate, and chlorinated further via a Pummerer rearrangement. These reactions produce a key intermediate in our new approach to the oxathiolane core used to prepare the antiretroviral medicines emtricitabine and lamivudine. During batch scale-up to tens of grams, we found that the sequence featured a strong exotherm and evolution of hydrogen chloride and sulfur dioxide. Keeping gaseous byproducts in solution and controlling the temperature led to better outcomes. These reactions are ideal candidates for implementation in a continuous mesoscale system for the sake of superior control. In addition, we found that fast reagent additions at controlled temperatures decreased byproduct formation. Herein we discuss the flow implementation and the final reactor design that led to a system with a 141 g/h throughput.
Kinetics of Chromic Acid Oxidation of Aliphatic Acetals in Aqueous Acetic Acid Medium
Ahamed, K. A. Basheer,Nambi, K.,Arulraj, S. J.
, p. 672 - 674 (2007/10/02)
The oxidation of aliphatic acetals (prepared from aliphatic aldehydes, aliphatic alcohols, halogen substituted alcohols and aromatic alcohols) by chromic acid in aqueous acetic acid medium is first order each in and and yields the corresponding ester as the main product.Substituent effect, activation parameters and salt effects suggest that the elimination of a proton from the complex species involving the acetal and chromium is the rate-determining step.The activation enthalpies and entropies of the reactions are linearly related.