Reaktion #451909

Reaktionsgleichung

piperidinecarboxaldehyde

6-aminopenicillanic acid

diisopropylethylamine

→

3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Lösungsmittel

CHCl3

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat room temperature for 3 hrs
2. 2
   SonstigeAfter the reaction
3. 3
   Sonstigethe solvent was removed
4. 4
   workup.DISSOLUTIONthe residue dissolved in water (40 ml)
5. 5
   WaschenThe aqueous solution, washed with diethyl ether
6. 6
   Sonstigepurified on Sephadex LH 20 column

Vorschrift

A mixture of 4-[3-(1H-imidazol-1-yl)propyl]-piperidine (1.5 g, 0.0078M) and dimethylformamide dimethylacetal (10 ml) was heated at 100° C. for 16 hrs. The excess of dimethylformamide dimethylacetal was removed to give 4-[3-(1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde dimethylacetal. To the mixture of 6-aminopenicillanic acid (1.16 g, 0.0053M) and diisopropylethylamine (1.03 ml) in dry CHCl3 (9 ml) was added the above piperidinecarboxaldehyde in CHCl3 (5 ml) at 0° C. and stirred at that temperature for 1 hr, then at room temperature for 3 hrs. After the reaction, the solvent was removed and the residue dissolved in water (40 ml). The aqueous solution, washed with diethyl ether, was adjusted to pH 3 with dilute aqueous HCl and purified on Sephadex LH 20 column to give [2S-(2alpha,5alpha,6beta)]-6-[[4-[3-(1 H-imidazol-1-yl)propyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1.2 mole hydrochloride monohydrate (0.87 g, 39% yield).

Quelle