Meropenem → Meropenem Trihydrate

HRID 1467351Notes

Reaction equation

HRID 1467351 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]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:12]2)=[C:8]([C:21]([OH:23])=[O:22])[N:7]2[C@H:3]1[C@@H:4]([C@H:24]([OH:26])[CH3:25])[C:5]2=[O:6]>O>[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([C:16]([N:18]([CH3:19])[CH3:20])=[O:17])[CH2:12]2)=[C:8]([C:21]([OH:23])=[O:22])[N:7]2[C@H:3]1[C@@H:4]([C@H:24]([OH:26])[CH3:25])[C:5]2=[O:6].[OH2:6].[OH2:6].[OH2:6]

Participants

3

Reactant 1

HCID 441130Meropenem

Product 1

HCID 441129Meropenem Trihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Crude meropenem (30 g) (meropenemic acid: 0.37%; meropenem dimer: 0.56%; total impurity content excluding meropenemic acid and meropenem dimer: 0.80%) was dissolved in de-ionized water (450 ml) pre-heated to 68° C. to 70° C. in a round bottom flask. The solution obtained was cooled to 20° C. to 25° C. over 25 minutes to 30 minutes, treated with carbon, filtered and cooled to 5° C. Meropenem trihydrate seed (0.075 g) was added at 5° C. and subjected to aging for 2 hours at 0° C. to 5° C. Acetone (150 ml) was added at −2° C. to 5° C. and the mixture was subjected to aging for further 3 hours at 0° C. to 5° C. The mixture was filtered and washed with acetone (150 ml) and dried for 5 hours to 8 hours at 36° C. to 38° C. under vacuum to obtain the title compound.

Workup

  1. temperaturepre-heated to 68° C. to 70° C. in a round bottom flask
  2. customThe solution obtained
  3. temperaturewas cooled to 20° C. to 25° C. over 25 minutes to 30 minutes
  4. additiontreated with carbon
  5. filtrationfiltered
  6. additionMeropenem trihydrate seed (0.075 g) was added at 5° C.
  7. additionAcetone (150 ml) was added at −2° C. to 5° C.
  8. waitto aging for further 3 hours at 0° C. to 5° C
  9. filtrationThe mixture was filtered
  10. washwashed with acetone (150 ml)
  11. customdried for 5 hours to 8 hours at 36° C. to 38° C. under vacuum

Sources & evidence

ORD record
ord-647a30383c1a4d71ab797ef01af02950
Source dataset
uspto-grants-2015_04
Patent number
US09000150B2

Reaction notes

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