Abstract
The greenness and sustainability of three different routes for the synthesis of an advanced intermediate for a group of HIV protease inhibitors used in antiretroviral (ARV) therapy are compared.
Highlights
Since the onset of the HIV-AIDS epidemic in 1981, 76.10 million people have been infected globally by the human immunodeficiency virus (HIV), with sub-Saharan Africa accounting for two-thirds of this total.[1]
Route A (Scheme 1)[13] made use of an enantio- and diastereoselective crossed aldol reaction between 4-butyloxy-1-butanal (2) and polymeric ethyl glyoxylate (3) in the presence of 3 mol% (S)-diphenylprolinol (4) to give aldol product 5, which was protected as the acetal derivative 6 before isolation
The authors went on to improve the product ee through crystallisation to produce a carbonate-derived product salt, our assessment ended at the point of the bis-THF
Summary
Since the onset of the HIV-AIDS epidemic in 1981, 76.10 million people have been infected globally by the human immunodeficiency virus (HIV), with sub-Saharan Africa accounting for two-thirds of this total.[1]. For each synthetic pathway, (i) waste generation (E-factor),[14,18] (ii) greenness relative to industrial benchmarks following the innovative Green Aspiration Level (iGALTM) methodology,[19,20] (iii) solvent intensity and nature according to the GSK solvent guide,[21] and (iv) score according to the Green MotionTM methodology of MANE.[22] Notwithstanding the importance of process greenness, in order to be sustainable a process must be cost-effective and this is determined by, inter alia, the cost of raw materials and solvents and the number of unit operations. Metrics and assessment tools provide chemists and chemical engineers with guidelines and measures that aid in developing safer and less impactful products and processes. Examples of web-based tools and guides that are used in a conceptual design stage to assess process greenness are the iGALTM and associated green scorecards, Green MotionTM, and the GSK solvent sustainability guide
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