Reaktion #1971582
ord-1263484844fe47e0bc3e6b9f2fed4d91
Reaktionsgleichung
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Vorschrift
Microanalyses were carried out by MEDAC Ltd., Brunel University, Uxbridge, U.K. Amino acid analyses were performed at the Department of Biochemistry, University of Cambridge, using a Pharmacia AlphaPlus Analyser with ninhydrin detection. 1H NMR spectra were determined in CDCl3 with tetramethylsilane as internal standard unless otherwise stated on JEOL FX90Q, Bruker AM 400WB or Varian Unity Plus 500 spectrometers. The 13C NMR spectrum was determined on a Bruker AM 400WB spectrometer. Positive ion FAB mass spectra at high resolution were obtained on a VG ZAB-SE instrument and negative ion spectra at low resolution were obtained by nanoelectrospray on a Thermoquest LCQ ion trap instrument. IR spectra were in Nujol mulls unless otherwise specified. Merck 9385 silica gel was used for flash chromatography. Organic extracts were dried over Na2SO4 and solvents were evaporated under reduced pressure. Sodium or ammonium phosphate buffer solutions were prepared from NaH2PO4.2H2O or NH4H2PO4 at the specified molarities in water and adjusted to the required pH value with 2 M aq. NaOH. HPLC data were obtained on Waters equipment using a reverse-phase column [Merck Lichrosphere RP8 column (Cat. No. 50832)]. UV detection was with a Waters 484 detector at 254 nm. Preparative HPLC was performed on a 2×30 cm column (Waters C18 packing material, Cat. No. 20594). 1-Acetylindoline (20) and 1-acetyl-5-bromoindoline (21) were prepared by literature methods. 5-Bromoindoline (22) was obtained by acidic methanolysis of 1-acetyl-5-bromoindoline (cf preparation of 12). 1,5-Diacetylindoline was prepared as described (23) but using 1,2-dichloroethane instead of carbon disulfide as solvent. 1-(2-Nitrophenylethyl) phosphate (24) was prepared as described (25). 4-Methoxyindole was prepared as described (26), reduced to 4-methoxyindoline as described (27) and acetylated to give 1-acetyl-4-methoxyindoline (28). N,N-Dimethyl-2-methyl-3-nitroaniline was prepared by a modification of a previously described method (29). Amberlite XAD-2 resin (Merck) was purified before use by exhaustive extraction with ethanol in a Soxhlet thimble, until the UV spectrum of the extract showed no absorption.