Water → HCID 86753164, compound

Participants

Reaction Steps

103 mg (0.726 mmol) of methyl iodide and 110 mg (0.726 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added while cooling with ice to a solution of 430 mg (0.66 mmol) of 5-(4-benzyloxycarbonylmethyl-6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-10-yl)-5-oxo-pentanoic acid in 15 ml of N,N-dimethylformamide. The reaction mixture was stirred firstly at room temperature and then at 40°, then cooled and finally poured into water and ethyl acetate. The organic phase was extracted twice with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying, 390 mg (88%) of methyl 5-(4-benzyloxycarbonylmethyl-6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-10-yl)-5-oxo-pentanoate were obtained as a white amorphous foam. MS (FAB): 664 (M+).

Provenance & Evidence