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|Title:||Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU|
|Authors:||Sureshbabu, Vommina V|
Sudarshan, N S
|Keywords:||N-Fmoc-β-amino alcohols;Bsmoc-β-amino alcohols;HATU|
|Abstract:||The activation of the Nα-urethane protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5-b]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated –OAt ester with NaBH4 results in the corresponding β-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of β-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.|
|Appears in Collections:||IJC-B Vol.48B(04) [April 2009]|
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