Marcellomycin → 21288-61-9

HRID 343649Notes

Reaction equation

HRID 343649 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, 0.1N) 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-2c1eaca70cb548aa8ebe3f8620f573de
Source dataset
uspto-grants-1999_01
Patent number
US05861492

Reaction notes

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