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Volumn 44, Issue 2, 2003, Pages 229-232

Facile synthesis and cleavage of imidazolidines in a novel protection strategy for the preparation of peptides containing a reduced amide bioisostere

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; DICHLOROMETHANE; FORMALDEHYDE; GLYCINAMIDE; IMIDAZOLIDINE DERIVATIVE; MONTMORILLONITE; PEPTIDE;

EID: 0037421081     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02562-5     Document Type: Article
Times cited : (9)

References (31)
  • 3
    • 0024582415 scopus 로고
    • and references cited therein
    • Stoit A.R., Pandit U.K. Tetrahedron. 45:1989;849-854. and references cited therein.
    • (1989) Tetrahedron , vol.45 , pp. 849-854
    • Stoit, A.R.1    Pandit, U.K.2
  • 22
    • 84992267652 scopus 로고    scopus 로고
    • Typical procedure for the formation of imidazolidines: To a solution of substrate monoalkoxycarbonyl diamine (1 mmol) in anhydrous THF (5 mL) was added at room temperature Montmorillonite KSF (400 mg) followed by aqueous 37% formaldehyde (3 mmol). The reaction mixture was stirred at room temperature for 1 h or until the starting material disappeared as monitored by TLC. After filtration, the solvent was removed in vacuo and residue was subjected to flash column chromatography to afford the desired imidazolidine
    • Typical procedure for the formation of imidazolidines: To a solution of substrate monoalkoxycarbonyl diamine (1 mmol) in anhydrous THF (5 mL) was added at room temperature Montmorillonite KSF (400 mg) followed by aqueous 37% formaldehyde (3 mmol). The reaction mixture was stirred at room temperature for 1 h or until the starting material disappeared as monitored by TLC. After filtration, the solvent was removed in vacuo and residue was subjected to flash column chromatography to afford the desired imidazolidine.
  • 23
    • 84992249694 scopus 로고    scopus 로고
    • +, 28%)
    • +, 28%).
  • 27
    • 84992291284 scopus 로고    scopus 로고
    • note
    • +, 20%).
  • 29
    • 0023150034 scopus 로고
    • Amino acids other than glycine have shown to undergo successfully reductive alkylation in both solution and solid phase. (a) Sasaki, Y.; Coy, D. H. Peptides 1987, 8, 119-121; (b) Martinez, J.; Bali, J.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Ligon, M. J. Med. Chem. 1985, 28, 1874-1879; © Pennighton, M. W. In: Peptide Synthesis Protocols; Pennington, M. W.; Dunn, B. M., Ed. Totowa, NJ; Humana Press; 1994, pp. 241-247.
    • (1987) Peptides , vol.8 , pp. 119-121
    • Sasaki, Y.1    Coy, D.H.2
  • 30
    • 0022405729 scopus 로고
    • Amino acids other than glycine have shown to undergo successfully reductive alkylation in both solution and solid phase. (a) Sasaki, Y.; Coy, D. H. Peptides 1987, 8, 119-121; (b) Martinez, J.; Bali, J.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Ligon, M. J. Med. Chem. 1985, 28, 1874-1879; © Pennighton, M. W. In: Peptide Synthesis Protocols; Pennington, M. W.; Dunn, B. M., Ed. Totowa, NJ; Humana Press; 1994, pp. 241-247.
    • (1985) J. Med. Chem. , vol.28 , pp. 1874-1879
    • Martinez, J.1    Bali, J.2    Rodriguez, M.3    Castro, B.4    Magous, R.5    Laur, J.6    Ligon, M.7
  • 31
    • 0011932208 scopus 로고
    • Pennington, M. W.; Dunn, B. M., Ed. Totowa, NJ; Humana Press
    • Amino acids other than glycine have shown to undergo successfully reductive alkylation in both solution and solid phase. (a) Sasaki, Y.; Coy, D. H. Peptides 1987, 8, 119-121; (b) Martinez, J.; Bali, J.; Rodriguez, M.; Castro, B.; Magous, R.; Laur, J.; Ligon, M. J. Med. Chem. 1985, 28, 1874-1879; © Pennighton, M. W. In: Peptide Synthesis Protocols; Pennington, M. W.; Dunn, B. M., Ed. Totowa, NJ; Humana Press; 1994, pp. 241-247.
    • (1994) Peptide Synthesis Protocols , pp. 241-247
    • Pennighton, M.W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.