HCID 178435494, compound → HCID 178435492, compound

Participants

Reaction Steps

Methyl pheophorbide-a (1, 1.0 g) was obtained from alga Spirulina destridratada by following the procedure described in K. M. Smith, D. A. Golf and D. J. Simpson, J. Am. Chem. Soc, 1985, 107, 4941-4954; and R. R. Pandey, D. A. Bellnier, K. M. Smith and T. J. Dougherty, Photochem. Photobiol, 1991, 53, 65-72 both of which are incorporated herein by reference The methyl pheophorbide-a was heated under reflux in collidine (100 ml) for 90 min during slow passage of a stream of nitrogen. See G. W. Kenner, S. W. McCombie and R. M. Smith. J. Chem. Soc. Perkin Trans. 1973, 1, 2517-2523, incorporated herein by reference. The solution is evaporated (0.1 mm Hg) and the residue was recrystallized from dichloromethane/methanol. Yield 820 mg; 91%, m.p. 217-219° C. lit. 220-225° C.; H. Fisher and A. Stern, Die Chemie des Pyrrole, vol II, Part 2, pp. 64 and 74, Akademische Verlag, Leipzig incorporated herein by reference. Vis: (max) 410 (112 000); 508 (11 000); 536 (9 600) 610 (8 200) 666 (45 000); NMR, ppm; 9.50. 9.38, 8.52 each s, 3H, 3 meso. H); 7.95-8.05 (m, 1H, CH═CH2); 6.30 and 6.15 (each s, 1H, CH-CH2), 5.27 to 5.12 (q, 2H, 10-CHz); 4.50 (m, 8-HO; 4.28 (m, 7-H); 3.70 (q, 2H, CH2CH2) 3.68 (s, 3H, CHCHCO2CH3); 3.62, 3.40, 3.22(each s, 3H, 3CH3); 2.70 (7a-H); 2.31(7a′-H); 2.56 (7b-H); 2.29 (7b′-H); 1.82 (d, 3H, 8-CH3); 1.70 (t, 3H, CH3CH3); −1.70 (s, 2

Provenance & Evidence