4-des-dimethylaminotetracycline → HCID 71306420, compound

HRID 256523Notes

Reaction equation

HRID 256523 reaction equation
[CH3:1][C@@:2]1([OH:29])[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:16]=2[C:15]([OH:23])=[C:14]2[C@@H:3]1[CH2:4][C@@H:5]1[C@:11](O)([C:12]2=[O:13])[C:10]([OH:25])=[C:9]([C:26]([NH2:28])=[O:27])[C:7](=[O:8])[CH2:6]1>N.[Zn]>[CH3:1][C@@:2]1([OH:29])[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:16]=2[C:15]([OH:23])=[C:14]2[C@@H:3]1[CH2:4][C@@H:5]1[C@H:11]([C:12]2=[O:13])[C:10]([OH:25])=[C:9]([C:26]([NH2:28])=[O:27])[C:7](=[O:8])[CH2:6]1

Participants

4

Reactant 1

HCID 546791824-des-dimethylaminotetracycline

Product 1

HCID 71306420HCID 71306420, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 222AmmoniaSolvent

Procedure

A solution was prepared by dissolving 20.0 g (50 mmoles) of 4-dedimethylaminotetracycline in 500 ml of a 15% aqueous ammonia solution. To the resulting solution 40 g of zinc dust was added and the mixture was vigorously stirred. After being stirred for twenty two (22) 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, washed with water, dried, and then purified and isolated by column chromatography, to provide 3.5 g of 4-dedimethylamino-12a-deoxytetracycline (yield: 18%) as a mixture of 2 isomers. The mixture was separated by HPLC to give isomer-A and isomer-B. Their properties are shown below.

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. washwashed with water
  7. customdried
  8. custompurified
  9. customisolated by column chromatography

Sources & evidence

ORD record
ord-3f4eaabd4482441baf11de43669a13fe
Source dataset
uspto-grants-1993_11
Patent number
US05258371

Reaction notes

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