Marcellomycin → 21288-61-9

HRID 482116Notes

Reaction equation

HRID 482116 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-ef4da3a012d44c91afe97292802f5e03
Source dataset
uspto-grants-1998_08
Patent number
US05792839

Reaction notes

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