Sodium Sulfate → Sulfurmycinone

HRID 1065254Notes

Reaction equation

HRID 1065254 reaction equation
C[C@@H]1O[C@@H]([O:8][C@@H:9]2[C:14]3[C:15]([OH:30])=[C:16]4[C:23](=[O:24])[C:22]5[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=5[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[C@@H:12]([C:31]([O:33][CH3:34])=[O:32])[C@@:11]([OH:39])([CH2:35][C:36]([CH3:38])=[O:37])[CH2:10]2)C[C@H](N(C)C)[C@@H]1O[C@@H]1O[C@@H](C)[C@@H](O[C@@H]2O[C@@H](C)C(=O)CC2)[C@@H](O)C1.S([O-])([O-])(=O)=O.[Na+].[Na+]>Cl>[CH3:38][C:36]([CH2:35][C@:11]1([OH:39])[C@H:12]([C:31]([O:33][CH3:34])=[O:32])[C:13]2[CH:18]=[C:17]3[C:19](=[O:20])[C:21]4[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[C:22]=4[C:23](=[O:24])[C:16]3=[C:15]([OH:30])[C:14]=2[C@@H:9]([OH:8])[CH2:10]1)=[O:37]

Participants

4

Reactant 2

HCID 24436Sodium SulfateHCID 155836Sulfurmycin A

Product 1

HCID 196522SulfurmycinoneYield 61%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 100 mg of sulfurmycin A in 20 ml of 0.1 N hydrochloric acid was heated at 90° C. for 60 minutes. The mixture was cooled and extracted with 40 ml of ethyl acetate. The ethyl acetate layer obtained was dehydrated over sodium sulphate and concentrated in vacuo to give 45 mg. of a yellow powder. Crystallisation from n-hexane/chloroform gave 32 mg of sulfurmycinone (yellow needles).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 40 ml of ethyl acetate
  3. customThe ethyl acetate layer obtained
  4. concentrationconcentrated in vacuo
  5. customto give 45 mg
  6. customCrystallisation from n-hexane/chloroform

Sources & evidence

ORD record
ord-496c8865c65f46a9a3b9faf547acb63e
Source dataset
uspto-grants-1982_05
Patent number
US04329339

Reaction notes

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