Sodium Hydroxide → Ertapenem disodium

HRID 2068128Notes

Reaction equation

HRID 2068128 reaction equation
[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([C:16]([NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[CH:24]=3)=[O:17])[CH2:12]2)=[C:8]([C:28]([OH:30])=[O:29])[N:7]2[C@H:3]1[C@@H:4]([C@H:31]([OH:33])[CH3:32])[C:5]2=[O:6].[Na].[OH-].[Na+:36]>C(=O)(O)[O-].[Na+]>[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([C:25]([O-:27])=[O:26])[CH:22]=[CH:21][CH:20]=3)=[O:17])[CH2:12]2)=[C:8]([C:28]([O-:30])=[O:29])[N:7]2[C@H:3]1[C@@H:4]([C@H:31]([OH:33])[CH3:32])[C:5]2=[O:6].[Na+:36].[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 665981361-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,3-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, monosodium salt, (4R,5S,6S)-

Product 1

HCID 150611Ertapenem disodium

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To the solution of sodium bicarbonate (2.5 g in 70 mL water) Ertapenem monosodium (15 g) was slowly added at 0-5° C., by maintaining pH around 7.5 using sodium hydroxide solution. The solution obtained was subjected to carbon treatment, followed by stirred with alumina and filtered. To filtrate, containing Ertapenem disodium was filtered through 0.2 micron filter paper and added into 2500 mL of cold IPA solution at 0-5° C. The solid obtained was filtered washed with IPA followed by acetone and IPE, dried under dry and wet nitrogen to yield Ertapenem disodium (Yield—8-12 g; sodium content: 9.2-10.5%; moisture content: 5-7%; pH: 7.5-8.0). The color of the reconstituted product was pale yellow.

Workup

  1. temperatureby maintaining pH around 7.5
  2. customThe solution obtained
  3. filtrationfiltered
  4. additionTo filtrate, containing Ertapenem disodium
  5. filtrationwas filtered through 0.2 micron
  6. filtrationfilter paper
  7. additionadded into 2500 mL of cold IPA solution at 0-5° C
  8. customThe solid obtained
  9. filtrationwas filtered
  10. washwashed with IPA
  11. customdried
  12. customunder dry

Sources & evidence

ORD record
ord-25eb0003c4a14a91b78c164bc984c6a8
Source dataset
uspto-grants-2012_10
Patent number
US08293924B2

Reaction notes

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