HCID 6335024, compound → Porphyrinogen

HRID 1417170Notes

Reaction equation

[B]1[B]C([B]B(C(OCC(OC(B(C2[B][B][B][B]2)[B]C2[B][B][B][B]2)=O)[C:18]2[C:40]3[NH:41][C:20](=[CH:21][C:22]4[NH:26][C:25]([CH:27]=[C:28]5[N:32]=[C:31]([CH:33]=[C:34]6[N:38]=[C:37]([CH:39]=3)[C:36](C)=[C:35]6CCC(O)=O)[C:30](CCC(O)=O)=[C:29]5C)=[C:24](C)[C:23]=4C(OC(B(C3[B][B][B][B]3)[B]C3[B][B][B][B]3)=O)COC(B(C3[B][B][B][B]3)[B]C3[B][B][B][B]3)=O)[C:19]=2C)=O)C2[B][B][B][B]2)[B][B]1.COC(=O)CC1C(CC(OC)=O)=CNC=1>C(Cl)Cl>[CH2:21]1[C:22]2[NH:26][C:25](=[CH:24][CH:23]=2)[CH2:27][C:28]2[NH:32][C:31](=[CH:30][CH:29]=2)[CH2:33][C:34]2[NH:38][C:37](=[CH:36][CH:35]=2)[CH2:39][C:40]2[NH:41][C:20]1=[CH:19][CH:18]=2

Participants

Conditions

Temperature: 25 °C

Procedure

A boronated porphyrin of the present invention, NiTCP, was synthesized using Lindsey's cyclization method as shown in Reaction Scheme 1. Pyrrole-3,4-diacetic acid dimethyl ester (prepared according to Chiusoli et al., 1989) in the amount of 79 mg and 3-o-carboranylmethyloxybenzaldehyde (prepared according to Miura et al., 1990) in the amount of 91 mg were dissolved in 20 ml of CH2Cl2 and then deoxygenated with nitrogen (N2) for 20 minutes. 15 μl of BF3.Et2O was added and then allowed to stir at 25° C. under N2 for approximately 1.5 hours to form an intermediate porphyrinogen.

Workup

customas shown in Reaction Scheme 1
customdeoxygenated with nitrogen (N2) for 20 minutes
addition15 μl of BF3.Et2O was added

Sources & evidence

ORD record: ord-dc435fdc5d3e4e7daa868f08896ba41f
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877165

Reaction notes

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