Synthesis of N-substituted peptide amides

Details Synthesis of N-substituted peptide amides Synthesis of N-substituted peptide amides

1983-10-24

1986-02-11

Phillips, Delbert R.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

2601125R, C08L 8900, C07C10352

Patent

active

045699674

ABSTRACT:
Peptide N-alkylamides, and other C-terminal N-substituted amides, can be synthesized using solid-phase synthesis on a benzene-containing resin which is suitably methylated. Reactive amino groups are attached directly or indirectly to the methyl groups, for example, such as by reacting commercially available chloromethylated polystyrene resins with an alkylamine to create a resin-amine. The C-terminal amino acid of the desired peptide is linked to the resin-amine via an amide linkage, and the peptide is thereafter built in normal fashion. Treatment of the completed peptide intermediate with HF is effective to both effect deprotection and cleave the peptide from the resin in the form of the N-substituted amide. Examples include peptide N-ethylamides, N-fluoroethylamide, N-anilides and other substituted N-benzylamides.

REFERENCES:
patent: 3778428 (1973-12-01), Mukaijama
patent: 4089821 (1978-05-01), Enkoji et al.
patent: 4101721 (1978-07-01), Rich et al.
patent: 4304692 (1981-12-01), Hughes et al.
Journal of Medicinal Chemistry, 1977, vol. 20, No. 11, pp. 1409-1412, Rivier, Lazarus, Perrin, Brown, "Neurotensin Analogues, Structure-Activity Relationships".
Synthetic Organic Chemistry (1955), p. 751.

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