Chloroform → HCID 131713388, compound

HRID 1388406Notes

Reaction equation

HRID 1388406 reaction equation
C[O:2]C(OC)N1CCC(CCCN2C(C)=C(C)N=C2C)CC1.[CH3:23][C:24]1([CH3:36])[S:28][C@@H:27]2[C@H:29](N)[C:30](=[O:31])[N:26]2[C@H:25]1[C:33]([OH:35])=[O:34].C(N(C(C)C)CC)(C)C.C(Cl)(Cl)[Cl:47]>>[ClH:47].[OH2:2].[CH3:23][C:24]1([CH3:36])[S:28][CH:27]2[N:26]([C:30](=[O:31])[CH2:29]2)[CH:25]1[C:33]([OH:35])=[O:34]

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 110826-Aminopenicillanic acidHCID 81531DiisopropylethylamineHCID 20239803HCID 20239803, compound

Product 1

HCID 131713388HCID 131713388, compoundYield 46%

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[3-(2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidine (0.75 g, 0.0032 M) and dimethylformamide dimethylacetal (20 ml) was heated at 100° C. for 9 hrs. The reaction was stripped to dryness to yield 4-[3-(2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidinecarboxaldehyde dimethylacetal. The solution of the above piperidine carboxaldehyde dimethylacetal in chloroform (4 ml) was then added to a mixture of 6-aminopenicillanic acid (0.67 g, 0.003 M) and diisopropylethylamine (0.47 ml) in chloroform (12 ml) at 0° C. The reaction was stirred at 0° C. for 1 hr and room temperature for 3 hrs. Solvent was removed and water (15 ml) was added. After being washed with diethyl ether, the aqueous solution, acidified to a pH 3 to about 3.5, was purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta)]-6[ [4-[3-[2,4,5-trimethyl-1H-imidazol-1-yl)propyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrate hydrochloride (0.71 g, 46% yield).

Workup

  1. customSolvent was removed
  2. additionwater (15 ml) was added
  3. washAfter being washed with diethyl ether
  4. customwas purified on Sephadex LH 20 columns

Sources & evidence

ORD record
ord-54898267db104db5bda542ae48dfd95b
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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