Meropenem → Meropenem Trihydrate

HRID 1467352Notes

Reaction equation

HRID 1467352 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]>CO>[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 887MethanolSolvent

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 methanol (120 mL) at 10° C. to 15° C. in a round bottom flask. The solution obtained was treated with carbon (10 g), filtered and cooled to about 10° C. to 15° C. followed by addition of meropenem trihydrate seed crystals (0.075 g) at 12° C. Isopropyl alcohol (200 ml) was added at 0° C. to 10° C. and the filtrate was subjected to aging for further 4 hours at 0° C. to 2° C. The mixture was filtered and washed with acetone (60 ml) and dried for 4 hours to 5 hours at 36° C. to 38° C. under vacuum to obtain the title compound.

Workup

  1. customThe solution obtained
  2. additionwas treated with carbon (10 g)
  3. filtrationfiltered
  4. temperaturecooled to about 10° C. to 15° C.
  5. additionfollowed by addition of meropenem trihydrate seed crystals (0.075 g) at 12° C
  6. additionIsopropyl alcohol (200 ml) was added at 0° C. to 10° C.
  7. filtrationThe mixture was filtered
  8. washwashed with acetone (60 ml)
  9. customdried for 4 hours to 5 hours at 36° C. to 38° C. under vacuum

Sources & evidence

ORD record
ord-f7576703c02a473580f0caf70766a615
Source dataset
uspto-grants-2015_04
Patent number
US09000150B2

Reaction notes

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