Tylosin → 4'-Dexydemycarosyltylosin

HRID 1086796

Reaction equation

HRID 1086796 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 mmol) of tylosin base in 80 ml of 0.2N hydrochloric acid are stirred for 4 hours at room temperature. The reaction medium obtained is washed with dichloromethane and the aqueous phase is separated and adjusted to pH 8.0. The latter phase is extracted twice with 120 ml of dichloromethane, and the organic phases are combined, dried over sodium sulfate and evaporated. The residue consists of demycarosyltylosin.

Workup

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

Sources & evidence

ORD record
ord-f6e4a531627649118b0dfd5e567e409d
Source dataset
uspto-grants-1991_07
Patent number
US05032581

Linked notes

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