Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.
[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.
Bunch
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Center for Drug Design and Transport, Department of Medicinal Chemistry, Royal Danish School of Pharmacy, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
Norrby
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PO
Frydenvang
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Krogsgaard-Larsen
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P
Madsen
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U
D005563:Formic Acid Esters / Q000737:chemistry*; D018698:Glutamic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D011789:Quantum Theory; D014961:X-Ray Diffraction
D005563:Formic Acid Esters; D011758:Pyrroles; C431590:pyroglutaminol; C000345:t-butyloxycarbonyl group; D018698:Glutamic Acid