Ion-exchange resins for solution phase parallel synthesis of chemical libraries

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 513-516

  Gayo, Leah M ^a   Suto, Mark J ^a  

^a CELGENE CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ION EXCHANGE RESIN; REAGENT; RESIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; EXTRACTION; TECHNIQUE;

EID: 0031021840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02362-3     Document Type: Article

References (8)

1. Selway, C. N.; Terett, N. K. Bioorg. Med. Chem. Lett., 1996, 4, 645.
2. Parlow, J. J. Tetrahedron Lett., 1996, 37, 5257; Parlow, J. J. Tetrahedron Lett., 1995, 36, 1395; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. Chem. Soc., Perkin Trans., 1980, 11, 2516.
3. Parlow, J. J. Tetrahedron Lett., 1996, 37, 5257; Parlow, J. J. Tetrahedron Lett., 1995, 36, 1395; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. Chem. Soc., Perkin Trans., 1980, 11, 2516.
4. Parlow, J. J. Tetrahedron Lett., 1996, 37, 5257; Parlow, J. J. Tetrahedron Lett., 1995, 36, 1395; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. Chem. Soc., Perkin Trans., 1980, 11, 2516.
5. 1H NMR and GCMS, and yields were determined.
6. General Procedure for the Preparation of 8: To Amberlite 68 (approximately 0.05 g dried under vaccum ovenight) was added the amine or alcohol (0.0475 mmol) in EtOAc (0.6 mL) followed by the acid chloride (0.050 mmol) in EtOAc (0.6 mL). The reaction mixture was then shaken overnight. Water (0.1 mL) was added, and the reaction shaken for an additional 30 minutes. Filtration and concentration of the filtrate provided 8 in high purities and yields as summarized in Table 2.
7. 2 (0.5 mL). After sonication for 1 hour, Amberlyst 15 (approximately 0.05 g) or Amberlite IRA®120 (plus) (approximately 0.05 g rinsed with EtOAc and dried under vaccum) was added, and the reaction mixture was sonicated for an additional 10 min. Filtration and concentration of the filtrate provided the title compound (0.0108 g, 92% yield) in 98% purity with all spectra in agreement with literature.
8. A paper describing the use of resins as scavengers was recently published: Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett., 1996, 37, 7193.