tert-Octylamine → Potassium Clavulanate

HRID 368551

Reaction equation

HRID 368551 reaction equation
C(N)(CC(C)(C)C)(C)C.[CH2:10]1[C:13](=[O:14])[N:12]2[C@@H:15]([C:21]([OH:23])=[O:22])/[C:16](/[O:20][C@H:11]12)=[CH:17]/[CH2:18][OH:19].C([O-])(=O)C.[K+:28]>C(O)C(C)C.O.C(O)(=O)C>[CH2:10]1[C:13](=[O:14])[N:12]2[C@@H:15]([C:21]([O-:23])=[O:22])/[C:16](/[O:20][C@H:11]12)=[CH:17]/[CH2:18][OH:19].[K+:28]

Participants

7

Reactant 3

HCID 61017tert-OctylamineHCID 517044Potassium Acetate2×HCID 5280980Clavulanic Acid2×

Product 1

HCID 23665591Potassium Clavulanate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6560IsobutanolSolvent2×

Procedure

5.5 g of the tert.octylamine salt of clavulanic acid are dissolved in 55 ml of iso-butanol containing 3.0% of water at a temperature of about 35°. 2.1 g of potassium acetate are dissolved in 55 ml of iso-butanol containing 0.25 ml of water and 0.2 ml of acetic acid. 6.0 ml of the potassium acetate solution are added dropwise to the solution of the clavulanic acid. 0.32 g of active carbon (Norit CG 1) are added. The suspension is stirred for ca. 15 minutes, filtrated and the filter is washed with 20 ml of iso-butanol. The solution is cooled to ca. 10° and the remaining solution of potassium acetate prepared as described above is added slowly. The mixture is cooled to ca. 5° and stirred for ca. 2 hours. A precipitate is formed which is filtrated off, washed with 30 ml of acetone and dried for about 20 hours in vacuo at ca. 45°. Potassium clavulanate is obtained (confirmed by 1H-NMR).

Workup

  1. addition0.32 g of active carbon (Norit CG 1) are added
  2. filtrationfiltrated
  3. washthe filter is washed with 20 ml of iso-butanol
  4. temperatureThe solution is cooled to ca. 10°
  5. customthe remaining solution of potassium acetate prepared
  6. additionabove is added slowly
  7. temperatureThe mixture is cooled to ca. 5°
  8. stirringstirred for ca. 2 hours
  9. customA precipitate is formed which
  10. filtrationis filtrated off
  11. washwashed with 30 ml of acetone
  12. customdried for about 20 hours in vacuo at ca. 45°

Sources & evidence

ORD record
ord-02fa1bbb40d44bf39642d35425cb9663
Source dataset
uspto-grants-2000_10
Patent number
US06133441

Linked notes

Loading…