Marcellomycin → 21288-61-9

HRID 636354Notes

Reaction equation

HRID 636354 reaction equation
[CH3:1][CH2:2][C@:3]1([OH:60])[C@H:25]([C:26]([O:28][CH3:29])=[O:27])[C:7]2[CH:8]=[C:9]3[C:21](=[O:22])[C:20]4[C:19]([OH:23])=[CH:18][CH:17]=[C:16]([OH:24])[C:15]=4[C:13](=[O:14])[C:10]3=[C:11]([OH:12])[C:6]=2[C@@H:5]([O:30][C@@H]2O[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@@H](O[C@@H]4O[C@@H](C)[C@@H](O)[C@@H](O)C4)[C@@H](O)C3)[C@@H](N(C)C)C2)[CH2:4]1>Cl>[CH3:1][CH2:2][C@:3]1([OH:60])[C@H:25]([C:26]([O:28][CH3:29])=[O:27])[C:7]2[CH:8]=[C:9]3[C:21](=[O:22])[C:20]4[C:15](=[C:16]([OH:24])[CH:17]=[CH:18][C:19]=4[OH:23])[C:13](=[O:14])[C:10]3=[C:11]([OH:12])[C:6]=2[C@@H:5]([OH:30])[CH2:4]1

Participants

3

Reactant 1

HCID 107861Marcellomycin

Product 1

HCID 15990821288-61-9

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

The drug (75 mg) is refluxed in methanolic HCl (25 mL, 0.1 N) for two hours. At the end of this Marcellomycin (75 mg, 0.175 mmol) is dissolved in methanolic HCl (25 mL, 0.1N) and refuxed at 50° C. for two hours. At the end of this time the reaction mixture is concentrated under vacuum and purified by preparative thin layer chromatography (15% methanol-chloroform). The aglycone ε-pyrromycinone is isolated as a bright red solid (21 mg, 54% yield).

Workup

  1. concentrationAt the end of this time the reaction mixture is concentrated under vacuum
  2. custompurified by preparative thin layer chromatography (15% methanol-chloroform)

Sources & evidence

ORD record
ord-4a5a0b1042e24efe8d0bd01b99d033c0
Source dataset
uspto-grants-2001_02
Patent number
US06194393B1

Reaction notes

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