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Synthesis 1989; 1989(11): 825-829
DOI: 10.1055/s-1989-27402
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Ring Cleavage of N-Acyl- and N-(Arylsulfonyl)histamines with Di-tert-butyl Dicarbonate. A One-Pot Synthesis of 4-Acylamino- and 4-Arylsulfonylamino-1,2-diaminobutanes

A. Warshawsky* , J. Altman, N. Kahana, R. Arad-Yellin, A. Deshe, H. Hasson, N. Shoef, H. Gottlieb
  • *Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot 76100, Israel
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Publication Date:
02 May 2002 (online)

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The ring cleavage of N-aryl- and N-(arylsulfonyl)histamines with di-tert-butyl dicarbonate in aqueous acetonitrile containing KOAc provides a one-pot synthesis of 4-acylamino- or 4-arylsulfonylamino-1,2-bis(tert -butoxycarbonylamino)butanes. Removal of the Boc groups in these protected triamines with trifluoroacetic acid or dry HCl in MeOH, followed by alkylation with benzyl bromoacetate, and then hydrogenation leads to N 4-acyl-1,2,4-butanetriamine -N 1,N 1,N 2,N 2 -tetraacetic acids and the N 4-arylsulfonyl analogs, respectively.