Reaktionsgleichung
[CH2:1]1[C:5]2=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[N:17]=[C:16]([CH:18]=[C:19]5[NH:24][C:22](=[CH:23][C:3](=[N:4]2)[CH2:2]1)[CH:21]=[CH:20]5)[CH2:15][CH2:14]4)=[CH:9][CH:8]=3.Br.IC1C=C(C=CC=1)CO.C([O-])([O-])=O.[K+].[K+]>>[CH2:9]1[C:10]2=[CH:12][C:13]3[NH:17][C:16]([CH:18]=[C:19]4[N:24]=[C:22]([CH:23]=[C:3]5[NH:4][C:5](=[CH:6][C:7](=[N:11]2)[CH2:8]1)[CH:1]=[CH:2]5)[CH:21]=[CH:20]4)=[CH:15][CH:14]=3Komponenten
Versuchsvorschrift
Bacteriohlorin 25: Following the procedure described for the synthesis of 16, treatment of 15 (50.0 mg, 0.0879 mmol, 1.0 equiv) with HBr gas, 3-iodobenzyl alcohol (0.1 mL), and K2CO3 (50.0 mg) resulted in the desired product. Purification was done by flash column chromatography (silica gel, 50% ethyl acetate in hexane). Yield: 42.8 mg, 62%. 1H NMR (400 MHz, CDCl3) δ: 8.52 (d, J=2.4 Hz, 1H, 10-H), 8.23 (s, 1H, 5-H), 8.05 (s, 1H, 20-H), 7.73 (d, J=21.6 Hz, 1H, Ph-H), 7.62 (d, J=7.6 Hz, 1H, Ph-H), 7.26 (1H, Ph-H, overlapping with the signal of CHCl3), 7.04 (t, J=8.0 Hz, 1H, Ph-H), 5.71 (q, J=6.4 Hz, 1H, 31-H), 4.97 (d, J=19.6 Hz, 1H, 132-H), 4.80 (d, J=19.6 Hz, 1H, 131-H), 4.46-4.63 (m, 2H, 31-OCH2), 4.11-4.19 (m, 2H, 7-H+18-H), 4.01 (d, 1H, 17-H), 3.88-3.90 (m, 1H, 8-H), 3.62 (s, 3H, COOCH3), 3.36 (s, 3H, 12-CH3), 3.15 (s, 3H, 2-CH3), 2.44-2.60 (m, 2H, 81-H+171-H), 2.11-2.34 (m, 3H, 171-CH2+171-H), 2.04 (d, J=6.4 Hz, 4H, 31-CH3+81-H), 1.65-1.77 (m, 6H, 7-CH3+18-CH3), 1.10-1.14 (m, 3H, 81-CH3), −0.22 (s, 1H, NH). MS (ESI) m/z: 785.4 (M++1). UV-vis, CH2Cl2, nm (ε): 720 (3.58×104), 659 (1.21×104), 602 (4.71×103), 517 (2.55×104), 486 (6.69×103), 456 (2.81×103), 382 (4.59×104), 353 (8.63×104).
Quellen und Nachweise
- ORD-Eintrag
- ord-82d1689e1bee4980aa0be6683e3dbbe1
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08679459B2
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