Erythromycin → 3-O-Methylmycarose

HRID 1088418Notes

Reaction equation

HRID 1088418 reaction equation
CC[C@H]1OC(=O)[C@H](C)[C@@H]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@@]1(O)C>Cl>[O:20]=[CH:21][CH2:22][C@:23]([C@H:24]([C@H:25]([CH3:27])[OH:26])[OH:28])([O:30][CH3:31])[CH3:29]

Participants

3

Reactant 1

HCID 12560Erythromycin

Product 1

HCID 54605883-O-MethylmycaroseYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Erythromycin A (Merck Index, 10th Edition Entry No. 3624) (50g) was dissolved in 1N aqueous hydrochloric acid (70 mL) and water (500 mL) and the mixture subjected to liquid-liquid extraction using diethyl ether for 99 h. The ether extract was evaporated to dryness to give L-cladinose (11.7 g, 97%) as a colorless viscous oil.

Workup

  1. extractionwater (500 mL) and the mixture subjected to liquid-liquid extraction
  2. customfor 99 h
  3. extractionThe ether extract
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-9bd319bce50f4dec8058b7266ed1858e
Source dataset
uspto-grants-1990_10
Patent number
US04962146

Reaction notes

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