Tylosin → 4'-Dexydemycarosyltylosin

HRID 2249146Notes

Reaction equation

HRID 2249146 reaction equation
[CH3:1][CH2:2][C@H:3]1[O:20][C:18](=[O:19])[CH2:17][C@@H:16]([OH:21])[C@H:15]([CH3:22])[C@@H:14]([O:23][C@@H:24]2[O:29][C@H:28]([CH3:30])[C@@H:27](O[C@@H]3O[C@@H](C)[C@H](O)[C@@](O)(C)C3)[C@H:26]([N:42]([CH3:44])[CH3:43])[C@H:25]2[OH:45])[C@@H:13]([CH2:46][CH:47]=[O:48])[CH2:12][C@@H:11]([CH3:49])[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH3:50])=[CH:5][C@@H:4]1[CH2:51][O:52][C@@H:53]1[O:58][C@H:57]([CH3:59])[C@@H:56]([OH:60])[C@@H:55]([O:61][CH3:62])[C@H:54]1[O:63][CH3:64]>Cl>[CH3:1][CH2:2][CH:3]1[O:20][C:18](=[O:19])[CH2:17][CH:16]([OH:21])[CH:15]([CH3:22])[CH:14]([O:23][CH:24]2[O:29][CH:28]([CH3:30])[CH2:27][CH:26]([N:42]([CH3:44])[CH3:43])[CH:25]2[OH:45])[CH:13]([CH2:46][CH:47]=[O:48])[CH2:12][CH:11]([CH3:49])[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH3:50])=[CH:5][CH:4]1[CH2:51][O:52][CH:53]1[O:58][CH:57]([CH3:59])[CH:56]([OH:60])[CH:55]([O:61][CH3:62])[CH:54]1[O:63][CH3:64]

Participants

3

Reactant 1

HCID 5280440Tylosin

Product 1

HCID 64419514'-Dexydemycarosyltylosin

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4 g (0.004 mole) of tylosin base are stirred in 80 ml of 0.2 N hydrochloric acid for 4 hours at ambient temperature. The reaction mixture obtained is washed with dichloromethane, the aqueous phase is separated and its pH adjusted to 8.0. The aqueous phase is extracted with twice 120 ml of dichloromethane and the organic phases are combined, dried over sodium sulphate and evaporated. The residue consists of demycarosyltylosin.

Workup

  1. customThe reaction mixture obtained
  2. washis washed with dichloromethane
  3. customthe aqueous phase is separated
  4. extractionThe aqueous phase is extracted with twice 120 ml of dichloromethane
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-436809198eba4f799faaabaaaed4be01
Source dataset
uspto-grants-1991_08
Patent number
US05043324

Reaction notes

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