HCID 178418840, compound → 12a-Deoxytetracycline

HRID 256524Notes

Reaction equation

HRID 256524 reaction equation
[CH3:1][C@:2]1([OH:32])[C@@H:16]2[C:11](=[C:12]([OH:30])[C@:13]3(O)[C:20](=[O:21])[C:19]([C:22]([NH2:24])=[O:23])=[C:18]([OH:25])[C@@H:17]([N:26]([CH3:28])[CH3:27])[C@@H:14]3[CH2:15]2)[C:9](=[O:10])[C:8]2[C:7]([OH:31])=[CH:6][CH:5]=[CH:4][C:3]1=2>N.[Zn]>[CH3:1][C:2]1([OH:32])[C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:31])[C:8]=2[C:9]([OH:10])=[C:11]2[CH:16]1[CH2:15][CH:14]1[CH:17]([N:26]([CH3:28])[CH3:27])[C:18]([OH:25])=[C:19]([C:22]([NH2:24])=[O:23])[C:20](=[O:21])[CH:13]1[C:12]2=[O:30]

Participants

4

Reactant 1

HCID 178418840HCID 178418840, compound

Product 1

HCID 5468010112a-DeoxytetracyclineYield 21%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 222AmmoniaSolvent

Procedure

A solution was prepared by dissolving 2 g of tetracycline in 50 ml of a 15% aqueous ammonia solution. To the resulting solution 4 g of zinc dust was added and the mixture was vigorously stirred. After being stirred for two (2) hours, the reaction mixture was filtered to remove excess zinc dust. The filtrate was neutralized with concentrated hydrochloric acid under ice-cooling. The precipitated solid was collected by filtration and then mixed with 450 ml of water. The mixture was adjusted to a pH of 1.8 by use of hydrochloric acid. The solution obtained was extracted with ether by liquid-liquid extraction method. The extract was concentrated to give 450 mg of crude product, which was recrystallized from dimethylformamide-methanol to yield 400 mg of 12a-deoxytetracycline (yield: 21%). HPLC revealed that this product was a mixture of two types of isomers, molecular weight FD mass [M]+ 428.

Workup

  1. customA solution was prepared
  2. filtrationthe reaction mixture was filtered
  3. customto remove excess zinc dust
  4. temperaturecooling
  5. filtrationThe precipitated solid was collected by filtration
  6. additionmixed with 450 ml of water
  7. customThe solution obtained
  8. extractionwas extracted with ether by liquid-liquid extraction method
  9. concentrationThe extract was concentrated
  10. customto give 450 mg of crude product, which
  11. customwas recrystallized from dimethylformamide-methanol

Sources & evidence

ORD record
ord-6ae5ca2aef874de5884963f7563b4ec1
Source dataset
uspto-grants-1993_11
Patent number
US05258371

Reaction notes

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