1-Butanol → HCID 6604391, compound

HRID 1076162Notes

Reaction equation

HRID 1076162 reaction equation
C(=O)(O)[O-].[Na+].CCCCCC.C(O)CCC.[CH3:17][C:18]1([CH3:48])[S:22][C@@H:21]2[C@H:23]([NH:26][C:27]([C@@H:29]([NH2:36])[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:28])[C:24](=[O:25])[N:20]2[C@H:19]1[C:37]([O:39][CH2:40][O:41][C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])=[O:43])=[O:38].Cl>O>[CH3:17][C:18]1([CH3:48])[S:22][C@@H:21]2[C@H:23]([NH:26][C:27]([C@@H:29]([NH2:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])[C:24](=[O:25])[N:20]2[C@H:19]1[C:37]([O:39][CH2:40][O:41][C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])=[O:43])=[O:38]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 76313488HCID 76313488, compound

Product 1

HCID 6604391HCID 6604391, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an efficiently stirred mixture of water (250 ml) containing sodium bicarbonate (10 g) and hexane (250 ml, boiling range 60°-80° C), n-butanol (15 ml) and crystalline seed (1 g) were added. Pivampicillin hydrochloride (50 g) dissolved in water (200 ml) was introduced over 1 hour at room temperature. The mixture was filtered and the residue washed with isopropanol-water (1:4) (250 ml), isopropanol (150 ml) and hexane (300 ml, bp. 60°-80° C). Air-drying at 25° C overnight yielded crystalline pivampicillin with a melting point of 114° C.

Workup

  1. additionwere added
  2. additionwas introduced over 1 hour at room temperature
  3. filtrationThe mixture was filtered
  4. washthe residue washed with isopropanol-water (1:4) (250 ml), isopropanol (150 ml) and hexane (300 ml, bp. 60°-80° C)
  5. customAir-drying at 25° C overnight

Sources & evidence

ORD record
ord-50af70ed06fd4cba8bf3ea5445fa822a
Source dataset
uspto-grants-1976_05
Patent number
US03956279

Reaction notes

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