6-Aminopenicillanic acid → HCID 12314047, compound

HRID 364727

Reaction equation

HRID 364727 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].C(N(C(C)C)CC)(C)C.N1(C=O)CCCCC1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[S:6][CH:5]2[N:4]([C:8](=[O:9])[CH2:7]2)[CH:3]1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 110826-Aminopenicillanic acidHCID 174291-PiperidinecarboxaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 12314047HCID 12314047, compoundYield 22,371.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  1. waitat room temperature for 3 hrs
  2. customAfter the reaction
  3. customthe solvent was removed
  4. dissolutionthe residue dissolved in water (40 ml)
  5. washThe aqueous solution, washed with diethyl ether
  6. custompurified on Sephadex LH 20 column

Sources & evidence

ORD record
ord-1880e61f9cc346b8afcdc0f324039003
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Linked notes

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