HCID 178459338, compound → HCID 178459337, compound

HRID 1018180Notes

Reaction equation

[CH2:1]([O:4][C:5]([C:7]1[C:8]2[NH:12][C:11]([CH:13]=[C:14]3[N:36]=[C:17]([C:18](C(OCCC)=O)=[C:19]4[NH:29][C:22](=[CH:23][C:24]5[CH:25]=[CH:26][C:27]=1[N:28]=5)[CH:21]=[CH:20]4)[CH:16]=[CH:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:2][CH3:3]>CN(C=O)C>[CH2:1]([O:4][C:5]([C:7]1[C:8]2[NH:12][C:11]([CH:13]=[C:14]3[N:36]=[C:17]([CH:18]=[C:19]4[NH:29][C:22](=[CH:23][C:24]5[CH:25]=[CH:26][C:27]=1[N:28]=5)[CH:21]=[CH:20]4)[CH:16]=[CH:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 145 °C

Procedure

To a magnetically stirred solution of porphyrin 31 (30 mg, 0.062 mmol) in anhydrous DMF (25 mL) was added MnCl2 (39 mg, 0.27 mmol). The reaction flask was fitted with a reflux condenser and the solution was heated to 145° C. for 2 h then exposed to a stream of air. The reaction mixture was heated for an additional 34 h then the solution was allowed to cool to room temperature for 48 h under a stream of air. Evaporation of DMF in vacuo provided a crude product that was adsorbed onto silica gel (2 g). Purification by column chromatography (gradient elution with 5→7.5% MeOH/CH2Cl2) provided 30 (35 mg; 98%) as a dark solid: mp>300° C.; UV-vis λmax=452. nm, ε=6.10×104 L/cm-mole; FAB MS m/z=535 [C28H24MnN4O4]+.

Workup

customThe reaction flask was fitted with a reflux condenser
temperatureThe reaction mixture was heated for an additional 34 h
temperatureto cool to room temperature for 48 h under a stream of air
customEvaporation of DMF in vacuo
customprovided a crude product that
customPurification
washby column chromatography (gradient elution with 5→7.5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-010e2b765bbe40e3abf3b0c07b857679
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479477B1

Reaction notes

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