Sodium Hydroxide → Ertapenem Sodium

HRID 2067709Notes

Reaction equation

HRID 2067709 reaction equation
C1N(CCCS(O)(=O)=O)CCOC1.[CH3:14][C@H:15]1[C:22]([S:23][C@@H:24]2[CH2:28][NH:27][C@H:26]([C:29]([NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([C:38]([OH:40])=[O:39])[CH:37]=3)=[O:30])[CH2:25]2)=[C:21]([C:41]([OH:43])=[O:42])[N:20]2[C@H:16]1[C@@H:17]([C@H:44]([OH:46])[CH3:45])[C:18]2=[O:19].[OH-].[Na+:48]>C(OCC)(=O)C>[CH3:14][C@H:15]1[C:22]([S:23][C@@H:24]2[CH2:28][NH:27][C@H:26]([C:29]([NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([C:38]([O-:40])=[O:39])[CH:37]=3)=[O:30])[CH2:25]2)=[C:21]([C:41]([OH:43])=[O:42])[N:20]2[C@H:16]1[C@@H:17]([C@H:44]([OH:46])[CH3:45])[C:18]2=[O:19].[Na+:48]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70807MopsHCID 150610Ertapenem2×

Product 1

HCID 23674512Ertapenem Sodium

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To MOPS buffer solution (prepared from 5.5 g MOPS in 100 mL water and pH adjusted to 6-8.5 with sodium hydroxide), diprotected Ertapenem of formula (IV) (10 g) was added and pH adjusted to 7.5 using aqueous sodium hydroxide solution. To this, ethyl acetate (100 mL) was added and stirred to get clear solution at 10-15° C. CO2 gas was purged for 20 mts. To this Pd/C (20 g, 10%) was added and subjected to hydrogenation with 4.5-5.0 Kg pressure at 5-10° C. After completion of reaction, the reaction mass was filtered and the layers separated. The aqueous layer was subjected to carbon treatment and the pH of the filtrate adjusted to 5.5-6.0 followed by stirring with THF (400 mL) for 10 h. The separated oily layer was slowly added into absolute ethanol (100 mL) under stirring at 5° C. The precipitated solid of ertapenem sodium was filtered, washed with ethanol and dried to yield amorphous form of ertapenem sodium. Dry weight: 4.0 g.

Workup

  1. additionwas added
  2. customto get clear solution at 10-15° C
  3. customCO2 gas was purged for 20 mts
  4. additionTo this Pd/C (20 g, 10%) was added
  5. customsubjected to hydrogenation with 4.5-5.0 Kg pressure at 5-10° C
  6. customAfter completion of reaction
  7. filtrationthe reaction mass was filtered
  8. customthe layers separated
  9. stirringby stirring with THF (400 mL) for 10 h
  10. additionThe separated oily layer was slowly added into absolute ethanol (100 mL)
  11. stirringunder stirring at 5° C
  12. filtrationThe precipitated solid of ertapenem sodium was filtered
  13. washwashed with ethanol
  14. customdried

Sources & evidence

ORD record
ord-b37a451e855f456092394a156aae9db8
Source dataset
uspto-grants-2012_10
Patent number
US08293894B2

Reaction notes

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