Resins for the Boc-/Bzl-Synthesis of Peptide Carboxamides

Chemfiles Volume 3 Article 4


Benzhydrylamine (BHA) and 4-methylbenzhydrylamine (MBHA) resins are developed for the Boc-/Bzl-synthesis of peptide carboxamides.(1,2) Due to the high stability of the amide bond, these resins have a broad application area as polymer basis for the immobilization of various linker systems carrying a carboxy functionality. Release of carboxamide products from MBHA resins can be achieved using either liquid HF at 0°C together with appropriate scavengers or trifluoromethanesulfonic acid (TFMSA).(2) Because cleavage of the peptide carboxamide products from a MBHA resin is effected under less drastic conditions, this support is particularly favorable. The MBHA resin is also used in the synthesis of quinolines via β-lactams,(3) 3,5-disubstituted hydantoins via resin-bound diamino acids,(4) piperazines and diketopiperazines from N-acylated amino acids,(5) 2-imidazolidones(6) and benzimidazoles.(7)

12106 Benzhydrylamine hydrochloride, polymer-bound, BHA resin•HCl PS cross-linked with 1% DVB
  capacity (amine): ~ 1.1 mmol/g resin particle size 200-400 mesh 10 g, 50 g
12110 Benzhydrylamine hydrochloride, polymer-bound, BHA resin•HCl PS cross-linked with 2% DVB
  capacity (amine): ~ 1.5 mmol/g resin particle size 100-200 mesh 5 g, 25 g
65835 4-Methylbenzhydrylamine, polymer-bound, MBHA resin PS cross-linked with 1% DVB
  capacity (amine): ~ 0.8 mmol/g resin particle size 100-200 mesh 1 g, 5 g
65836 4-Methylbenzhydrylamine hydrochloride, polymer-bound, MBHA resin•HCl PS cross-linked with 1% DVB
  capacity (amine): ~ 1.4 mmol/g resin particle size 200-400 mesh 10 g, 50 g
65837 4-Methylbenzhydrylamine hydrochloride, polymer-bound, MBHA resin•HCl PS cross-linked with 1% DVB
  capacity (amine): ~ 0.7 mmol/g resin particle size 100-200 mesh 10 g, 50 g

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Materials

     

References

  1. Pietta, P. G. et al. J. Org. Chem. 1974, 39, 44.
  2. Matsueda, G. R.; Stewart, J. M. Peptides 1981, 2, 45.
  3. Pei, Y. et al. Tetrahedron Lett. 1997, 38, 3349.
  4. Nefzi, A. et al. Tetrahedron Lett. 1998, 39, 8199.
  5. Nefzi, A. et al. Tetrahedron Lett. 1999, 40, 8539.
  6. Nefzi, A. et al. J. Comb. Chem. 1999, 1, 195.
  7. Smith, J. M.; Krchnák, V. Tetrahedron Lett. 1999, 40, 7633.

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