Abstract
(Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH3CN-H2O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH3CN-H2O (5:1) in the absence of base. Structures 7b, 7d and 8b, 8d are supported by 2D NMR spectroscopic methods including gDQCOSY, gHMQC, gHMBC, and 1H-15N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.
Original language | English (US) |
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Pages (from-to) | 7165-7167 |
Number of pages | 3 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 18 |
DOIs | |
State | Published - Sep 18 2009 |
Bibliographical note
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