6-Aminopenicillanic acid → Penicillanic Acid

HRID 2398724Notes

Reaction equation

HRID 2398724 reaction equation
[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[C@H:7](N)[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12]>O1CCCC1>[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 110826-Aminopenicillanic acid

Product 1

HCID 6891Penicillanic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 50 ml of anhydrous tetrahydrofuran were added 447 mg (1 mmol) of 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate and 216 mg (1 mmol) of 6-aminopenicillanic acid and the mixture was stirred at room temperature for 24 hours. The solvent was then distilled off under a reduced pressure and the residue was crystallized by the addition of dimethylformamide. Recrystallization from dimethylformamide gave colourless needles melting at 63° C. (uncorrected). Yield: 630 mg (95%).

Workup

  1. distillationThe solvent was then distilled off under a reduced pressure
  2. customthe residue was crystallized by the addition of dimethylformamide
  3. customRecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-a1cc556daef0439a804d62604f96acb2
Source dataset
uspto-grants-1977_05
Patent number
US04025622

Reaction notes

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