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Non-nucleophilic base (KHMDS) mediated nucleophilic conversion of Merrifield resin into aminomethyl resin

Non-nucleophilic base (KHMDS) mediated nucleophilic conversion of Merrifield resin into aminomethyl resin
Non-nucleophilic base (KHMDS) mediated nucleophilic conversion of Merrifield resin into aminomethyl resin
During a series of alkylation reactions on Merrifield resin involving a number of alkoxides, generated in situ by the treatment of alcohols with a variety of bases (NaH, LiHMDS, etc.), it was determined that treatment of the resin with a number of hexamethyldisilazide bases gave rise to high yields of aminomethyl resin, presumably by nucleophilic displacement of the chloride. The reaction was optimised as a simple one-step process for the generation of aminomethyl resin from chloromethyl polystyrene. The resulting resin was used to synthesise a tripeptide.
solid-phase synthesis, substitution, peptide
0040-4039
5517-5519
Sampson, David F. J.
a8b9436b-fe21-4145-b0cb-e731f6cf4b03
Simmonds, Robin G.
a649912a-8aa9-4464-a119-255b687f3e24
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
Sampson, David F. J.
a8b9436b-fe21-4145-b0cb-e731f6cf4b03
Simmonds, Robin G.
a649912a-8aa9-4464-a119-255b687f3e24
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900

Sampson, David F. J., Simmonds, Robin G. and Bradley, Mark (2001) Non-nucleophilic base (KHMDS) mediated nucleophilic conversion of Merrifield resin into aminomethyl resin. Tetrahedron Letters, 42 (32), 5517-5519. (doi:10.1016/S0040-4039(01)00994-7).

Record type: Article

Abstract

During a series of alkylation reactions on Merrifield resin involving a number of alkoxides, generated in situ by the treatment of alcohols with a variety of bases (NaH, LiHMDS, etc.), it was determined that treatment of the resin with a number of hexamethyldisilazide bases gave rise to high yields of aminomethyl resin, presumably by nucleophilic displacement of the chloride. The reaction was optimised as a simple one-step process for the generation of aminomethyl resin from chloromethyl polystyrene. The resulting resin was used to synthesise a tripeptide.

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Published date: 6 August 2001
Keywords: solid-phase synthesis, substitution, peptide

Identifiers

Local EPrints ID: 19616
URI: http://eprints.soton.ac.uk/id/eprint/19616
ISSN: 0040-4039
PURE UUID: 9ce2046b-46bb-487d-a89b-ae143aea5f70

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Date deposited: 13 Feb 2006
Last modified: 15 Jul 2019 19:26

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Contributors

Author: David F. J. Sampson
Author: Robin G. Simmonds
Author: Mark Bradley

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