Solid phase preparation of amines

Details Solid phase preparation of amines Solid phase preparation of amines

1998-10-07

1999-08-03

Tsang, Cecilia J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

5253322, 554154, C07K 104

Patent

active

059326964

ABSTRACT:
A method for the solid phase preparation of an amine by a novel synthesis is described where a diol is monoalkylated with a chloromethyl resin followed by reaction with N,N'-carbonyldimidazole to afford a resin-bound tertiary-alkoxycarbonyl-imidazole which is subsequently N-alkylated and then sequentially treated with appropriate building blocks and reagents to afford a resin-bound amine which affords the desired amine after treatment with an acid as well as other valuable intermediates used in the process.

REFERENCES:
patent: 5416193 (1995-05-01), Desai
patent: 5432263 (1995-07-01), Haviv et al.
patent: 5652336 (1997-07-01), Fife et al.
S. Wang and R. Merrifield, "Preparation of a 5-Alkyloxycarbonylhydrazide Resin and Its Application to Solid Phase Peptide Synthesis", J. Am. Chem. Soc., 1969, vol. 91, No. 23, pp. 6488-6491.
S. Wang, "Solid-Phase Synthesis of Protected Peptide Hydrazides. Preparation and Application of Hydroxymethyl Resin and 3-(p-Benzyloxyphenyl)-1,1-dimethylpropyloxycarbonylhydrazide Resin", J. Org. Chem., 1975, vol. 40, No. 9, pp. 1235-1239.

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