A Facile Synthesis of Chiral Isocyanate-phenol and Unsymmetrical Urea Derived from Tyrosines without Protecting Phenolic Hydroxyl Groups

Atsushi      Nagai; Bungo      Ochiai; Takeshi      Endo

doi:10.2174/1570178054406020

Abstract

A facile method for synthesis and isolation of chiral isocyanate-phenols, obtained from the reactions of L-tyrosine and L-DOPA [L-3-(3,4-dihydroxyphenyl)alanine] derivatives with di-tert-butyltricarbonate (DBTC), is described. Reaction of the obtained isocyanate-phenol with n-butylamine gave the corresponding chiral unsymmetrical urea.

Keywords: isocyanate, phenol, unsymmetrical, urea, tyrosine, dopa, di-tert-butyltricarbonate

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Letters in Organic Chemistry

Title: A Facile Synthesis of Chiral Isocyanate-phenol and Unsymmetrical Urea Derived from Tyrosines without Protecting Phenolic Hydroxyl Groups

Volume: 2 Issue: 5

Author(s): Atsushi Nagai, Bungo Ochiai and Takeshi Endo

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Keywords: isocyanate, phenol, unsymmetrical, urea, tyrosine, dopa, di-tert-butyltricarbonate

Abstract: A facile method for synthesis and isolation of chiral isocyanate-phenols, obtained from the reactions of L-tyrosine and L-DOPA [L-3-(3,4-dihydroxyphenyl)alanine] derivatives with di-tert-butyltricarbonate (DBTC), is described. Reaction of the obtained isocyanate-phenol with n-butylamine gave the corresponding chiral unsymmetrical urea.

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Nagai Atsushi, Ochiai Bungo and Endo Takeshi, A Facile Synthesis of Chiral Isocyanate-phenol and Unsymmetrical Urea Derived from Tyrosines without Protecting Phenolic Hydroxyl Groups, Letters in Organic Chemistry 2005; 2 (5) . https://dx.doi.org/10.2174/1570178054406020