Sodium Carbonate → Erythromycin ethyl succinate

HRID 1508608

Reaction equation

HRID 1508608 reaction equation
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([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:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[C:70]([O:77][CH2:78][CH3:79])(=[O:76])[CH2:71][CH2:72][C:73]([O-])=[O:74].[Br-].C(OCC)(=O)CCC([O-])=O>CCOCC.O>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([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:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[O:44][C:73]([CH2:72][CH2:71][C:70]([O:77][CH2:78][CH3:79])=[O:76])=[O:74])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 12560Erythromycin2×HCID 516892Sodium BicarbonateHCID 18404837HCID 18404837, compoundHCID 86718268Monoethyl succinate bromide

Product 1

HCID 443953Erythromycin ethyl succinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

The process for preparing erythromycin ethylsuccinate hydrate comprises: method A. in a reaction vessel, one or more of a C1-C6 lower alcohol, a C2-C6 lower nitrile, a C3-C8 lower ketone or C2-C8 lower ether is used as a solvent, to the solvent is added erythromycin, stirred at a temperature of 0-50° C. to dissolve erythromycin; to the solution is added sodium bicarbonate or sodium carbonate or potassium carbonate, and water, stirred, and cooled to 20° C. or below; to the cooled mixture is added monoethyl succinate halide, including monoethyl succinate chloride or monoethyl succinate bromide, allowed to react, and monitored by TLC until the reaction is complete; to the resultant is added an acid or a base to control the pH value at about 7.0-8.5; the organic phase is precipitated and separated; to the organic phase is added water, cooled to −20° C.-10° C.; upon the solid is precipitated completely, the mixture is filtered, the resulting solid is recrystalized with water and one or more of a C1-C6 lower alcohol, a C2-C6 lower nitrile, a C2-C8 lower ether, a C3-C8 lower ketone or C1-C6 lower halogenated hydrocarbons as solvent once or more times, cooled to −20° C.-10° C., filtered, dried to obtain erythromycin ethylsuccinate crystalline hydrate;

Workup

  1. stirringstirred
  2. temperaturecooled to 20° C. or below
  3. customto react
  4. additionto the resultant is added an acid
  5. customthe organic phase is precipitated
  6. customseparated
  7. additionto the organic phase is added water
  8. temperaturecooled to −20° C.-10° C.
  9. customupon the solid is precipitated completely
  10. filtrationthe mixture is filtered
  11. customthe resulting solid is recrystalized with water and one or more of a C1-C6 lower alcohol
  12. temperaturea C2-C6 lower nitrile, a C2-C8 lower ether, a C3-C8 lower ketone or C1-C6 lower halogenated hydrocarbons as solvent once or more times, cooled to −20° C.-10° C.
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-75738953660c40d2a5f43ae562378a52
Source dataset
uspto-grants-2015_12
Patent number
US09221862B2

Linked notes

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