1263-63-4 → Mesoporphyrin IX

HRID 713539Notes

Reaction equation

HRID 713539 reaction equation
[CH3:1][CH2:2][C:3]1[C:25]2[NH:26][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[N:17]=[C:16]([CH:18]=[C:19]5[N:23]=[C:22]([CH:24]=2)[C:21]([CH3:27])=[C:20]5[CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[C:15]([CH2:34][CH2:35][C:36]([O:38]C)=[O:37])=[C:14]4[CH3:40])=[C:9]([CH3:41])[C:8]=3[CH2:42][CH3:43])[C:4]=1[CH3:44]>[OH-].[NH4+]>[CH3:1][CH2:2][C:3]1[C:25]2[NH:26][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[N:17]=[C:16]([CH:18]=[C:19]5[N:23]=[C:22]([CH:24]=2)[C:21]([CH3:27])=[C:20]5[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:15]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[C:14]4[CH3:40])=[C:9]([CH3:41])[C:8]=3[CH2:42][CH3:43])[C:4]=1[CH3:44]

Participants

3

Reactant 1

HCID 791511263-63-4

Product 1

HCID 72422Mesoporphyrin IX

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

In some aspects, a method of synthesizing a metal mesoporphyrin compound comprises forming a protoporphyrin methyl ester from hemin and converting the protoporphyrin methyl ester intermediate to a metal mesoporphyrin compound through metal insertion and hydrogenation. In some embodiments, metal insertion yields a metal protoporphyrin dimethyl ester intermediate. In further embodiments, the metal protoporphyrin dimethyl ester is hydrogenated in dichloromethane over palladium catalyst to form a metal mesoporphyrin dimethyl ester. In embodiments, the metal mesoporphyrin dimethyl ester is heated in dilute ammonium hydroxide to form the metal mesoporphyrin compound. In embodiments, the metal may comprise tin, iron, zinc, chromium, manganese, copper, nickel, magnesium, cobalt, platinum, gold, silver, arsenic, antimony, cadmium, gallium, germanium, palladium, or the like. In some embodiments, tin is the inserted metal. In embodiments, tin is inserted into mesoporphyrin to make stannsoporfin using tin oxide, tin chloride, tin sulfate, tin bromide, tin oxalate, tin pyrophosphate hydrate, tin 2-ethylhexanoate, tin methanesulfonic acid, or tin trifluromethanesulfonate.

Sources & evidence

ORD record
ord-c93323c0d5624a90bb8399ea2b3fb1a0
Source dataset
uspto-grants-2015_11
Patent number
US09181285B2

Reaction notes

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