Triethylamine → 6-[5-(2-Oxo-Hexahydro-Thieno[3,4-D]Imidazol-4-Yl)-Pentanoylamino]-Hexanoic Acid

Beteiligte Stoffe

Reaktionsschritte

6-(Biotinylamino)caproic acid was prepared from N-hydroxysuccinimido biotinate (Jasiewicz et al., Exp. Cell Res. 100, pp 213-217 (1976)) and 6-aminocaproic acid methyl ester hydrochloride by a previously described method (Hofmann et al., Biochemistry 23, pp 2547-2553 (1984)). 6-(Biotinylamino)caproic acid chloride was prepared by incubating 6-(biotinylamino)caproic acid (0.36 g, 1 mmole) in 4 ml of thionyl chloride at 25°-35° C. for 1 h, and excess thionyl chloride was removed under reduced pressure. The residue was dissolved in DMF and 7-amino-4-chloro-3-(2-phenylethoxy)isocoumarin (0.34 g, 1 mmole) and Et3N (0.1 g, 1 mmole) were added and the reaction mixture was stirred at r.t. overnight. The product was purified from column chromatography and eluted with CH2Cl2 :MeOH=10:1, yield, 28%, mp 163°-167° C., NMR was consistent with the assigned structure, mass spectra (FAB+) m/e=655 (M+1). Anal. Calc. for C33H39N4O6ClS.H2O: C, 58.87; H, 6.14; N, 8.32; Cl, 5.27. Found: C, 58.72; H, 6.22; N, 8.90; Cl, 5.50.

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