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HomeChemistryMechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide through a one-pot sequential aminolysis-sulfation response of (S)-γ-hydroxymethyl-γ-butyrolactone...

Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide through a one-pot sequential aminolysis-sulfation response of (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO)


To valorize additional the extremely precious bio-based platform (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO), whose sustainable kiloscale-synthesis from cellulose-derived levoglucosenone (LGO) has been validated, a mechanochemical technique was developed to supply new potential bio-based surfactants underneath solventless circumstances. First, the response of 2H-HBO with major or secondary amines was investigated adopted by a sulfation response with the remoted N-alkyl-amide derivatives to acquire the corresponding N-alkyl sulfated compounds. The latter was then obtained by an optimized one-pot sequential aminolysis–sulfation in a planetary ball mill with glorious effectivity. For the primary time, sulfated compounds arising from bio-based/renewable sources had been obtained completely through a mechanochemical course of. Consequently, the sulfated derivatives of 2H-HBO had been fashioned quantitatively and remoted in 69–79% general yields. The crucial micelle focus (CMC) was decided for a few of them which exhibited fascinating anionic surfactant properties.

Graphical abstract: Mechanochemical synthesis of (4S)-N-alkyl-4,5-bis-sulfooxypentanamide via a one-pot sequential aminolysis-sulfation reaction of (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO)

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