Water → Chlorin

HRID 1190763

Reaction equation

[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.O>>[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]=3

Participants

Reactant 2

HCID 962Water

HCID 9548778Bacteriochlorin

Product 1

HCID 65106Chlorin

Procedure

Method B (from 16): Following the procedure described for the preparation of 6, treatment of 16 (40.0 mg, 0.0705 mmol, 1.0 equiv) with FeCl36.H2O (66.3 mg, 4.0 equiv) resulted in the desired product. Purification was done by flash column chromatography (silica gel, 3% acetone in CH2Cl2). Yield: 25.2 mg, 55%. 1H NMR (400 MHz, CDCl3) δ: 9.18 (s, 1H, 10-H), 9.03 (d, J=14 Hz, 1H, 5-H), 8.65 (s, 1H, 20-H), 5.79-5.86 (m, 1H, 31-H), 5.48 (d, 2H, 132-H), 4.41-4.50 (m, 1H, 8-H), 4.20-4.22 (m, 1H, 7-H), 3.90 (t, J=8.0 Hz, 2H, 17-CH2), 3.75 (s, 3H, COOCH3), 3.52-3.66 (m, 5H, 31-OCH2+12-CH3), 3.43 (d, J=3.6 Hz, 3H, 2-CH3), 3.23 (s, 3H, 18-CH3), 2.94 (t, J=8.0 Hz, 2H, 171-CH2), 2.42-2.52 (m, 1H, 81-H), 2.13-2.20 (m, 1H, 81-H), 2.10 (d, J=6.8 Hz, 3H, 31-CH3), 1.91/1.87 (d, J=7.2 Hz, 3H, 7-CH3), 1.66-1.76 (m, 3H, 31-OCH2CH2CH2CH2CH2CH3), 1.15-1.23 (m, 9H, 31-OCH2CH2CH2CH2CH2CH3+81-CH3), 0.78-0.81 (m, 3H, 31-OCH2CH2CH2CH2CH2CH3), −0.34 (br s, 1H, NH), −1.52 (br s, 1H, NH). MS (ESI) m/z: 651.4 (M++1). UV-vis, CH2Cl2, λmax nm (ε): 669 (4.45×104), 612 (6.77×103), 540 (6.77×103), 513 (1.11×104), 411 (7.82×104).

Sources & evidence

ORD record: ord-ca78a36cbcdc43d1a6a4372e95112f9f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08679459B2

Linked notes

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