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Synlett 1997; 1997(8): 998-1000
DOI: 10.1055/s-1997-944
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Reaction of Trimethylsilyl Benzhydryl Ethers with Methyl N-(Trimethylsilyl)pyroglutamate: an Easy and Rapid N-Alkylation

Benoît Rigo1 , Philippe Gautret2 , Anne Legrand2 , Jean-Pierre Hénichart3 , Daniel Couturier4
  • 1Laboratoire de Chimie Organique et Environnement, Ecle des Hautes Etudes Industrielles, 13, rue de Toul, 59046 Lille, France, Fax: (33) 03 20 42 81 46; e-mail: rigo@hei.fupl.asso.fr
  • 2Laboratoire de Chimie Organique et Environnement, Ecle des Hautes Etudes Industrielles, 13, rue de Toul, 59046 Lille, France
  • 3Institut de Chimie Pharmaceutique, Faculté de Pharmacie, 3, rue du Professeur Laguesse, 59006 Lille, France
  • 4Laboratoire de Chimie Organique et Environnement, Université des Sciences et Technologies de Lille, 59655 Villeneuve d’Ascq, France
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Publikationsdatum:
31. Dezember 2000 (online)

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In the presence of a small amount of catalyst (mainly triflic acid), methyl N-(trimethylsilyl)pyroglutamate quickly reacts with benzhydryl chlorides or preferentially with trimethylsilyl benzhydryl ethers to give methyl N-(benzhydryl)pyroglutamates in nearly quantitative isolated yields.

methyl N-(trimethylsilyl)pyroglutamate - benzhydryl silyl ethers - N-alkylation