HCID 178435494, compound → HCID 178435492, compound

HRID 2210592Notes

Reaction equation

HRID 2210592 reaction equation
[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[CH:34]([CH3:35])[CH:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH:27](C(OC)=O)[C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45]>N1C(C)=CC(C)=CC=1C>[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[C@@H:34]([CH3:35])[C@H:33]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:15]([C:16]5[CH2:27][C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45]

Participants

3

Reactant 1

HCID 178435494HCID 178435494, compound2×

Product 1

HCID 178435492HCID 178435492, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

Methyl pheophorbide-a (1, 1.0 g) was obtained from alga Spirulina destridratada by following the procedure described in K. M. Smith, D. A. Goff and D. J. Simpson, J. Am. Chem. Soc., 1985, 107, 4941-4954; and R. K. 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. Kenher, S. W. McCombie and K. 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-CH2); 4.50 (m, 8-HO; 4.28 (m, 7-H); 3.70 (q, 2H, CH2CH3); 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, CH2CH3); -1.70 (s, 2H,2 NH)

Workup

  1. customThe solution is evaporated (0.1 mm Hg)
  2. customthe residue was recrystallized from dichloromethane/methanol
  3. customlit. 220°-225° C.

Sources & evidence

ORD record
ord-a5add26d28c74546ba45b4aefd2c7a5a
Source dataset
uspto-grants-1995_10
Patent number
US05459159

Reaction notes

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