Sodium Hydroxide → 6-Aminopenicillanic acid

HRID 1076458Notes

Reaction equation

HRID 1076458 reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10]C(CC3C=CC=CC=3)=O)[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([O-:22])=[O:21].[K+].[OH-].[Na+]>O>[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23664709Penicillin G Potassium

Product 1

HCID 110826-Aminopenicillanic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 12 g of the wet treated immobilized cell preparation of Example 10 in 100 ml of water at pH 8.0 and 37°C is added 1 g of potassium penicillin G. The pH of the reaction is maintained at 8.0 by the monitored addition of 1N NaOH and the reaction is complete after about 3 hours. The immobilized cell material is filtered, washed with water and stored as a wet cake until further use. The filtrate is adjusted to pH 2 with 2N HCl and extracted with ethyl acetate. The resulting aqueous layer is adjusted to pH 4.3 with 2N NaOH, concentrated and cooled to give crystalline 6-APA.

Workup

  1. filtrationThe immobilized cell material is filtered
  2. washwashed with water
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated
  5. temperaturecooled

Sources & evidence

ORD record
ord-bba2b7f5ca7d48769ef9cc5d1217f804
Source dataset
uspto-grants-1976_05
Patent number
US03957580

Reaction notes

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