Dimethylformamide dimethyl acetal → HCID 20239749, compound
Reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH:15]1[CH2:19][CH2:18][N:17]=[C:16]1[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C[O-].[Na+].[CH3:29][O:30][CH:31]([O:35][CH3:36])N(C)C>CO>[CH3:29][O:30][CH:31]([O:35][CH3:36])[N:23]1[CH2:24][CH2:25][CH:20]([C:16]2[NH:17][CH2:18][CH2:19][N:15]=2)[CH2:21][CH2:22]1Participants
Procedure
A solution of the dihydrochloride salt of 4-(4,5-dihydro-1H-imidazol-2-yl)piperidine (0.99 g, 0.0044M) in methanol (10 ml) which contained sodium methoxide (0.009M) was stirred at room temperature for 10 minutes and dimethylformamide dimethylacetal (10 ml) was added and refluxed at 80° C. for 8 hrs. The excess of dimethylformamide dimethylacetal was removed to give 4-(4,5-dihydro-1H-imidazol-2-yl)-1-piperidinecarboxaldehyde dimethylacetal. To a mixture of 6-aminopenicillanic acid (0.785 g, 0.0035M) and diisopropyl ethylamine (0.412 ml) in dry chloroform was added the chloroform solution (30 ml) of the above piperidinecarboxaldehyde dimethyl acetal at 0° C. The reaction was stirred at 0° C. for 1 hr and at room temperature for 3 hrs. After this period, the solvent was removed in vacuo and the residue was dissolved in water (40 ml). The aqueous solution washed with ethylacetate was acidified to pH 3 with dil HCl and purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta)]-6-[[[4-(4,5-dihydro-1H-imidazol-2yl)-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrochloride (0.21 g, 11.5% yield).
Workup
- temperaturerefluxed at 80° C. for 8 hrs
- customThe excess of dimethylformamide dimethylacetal was removed
Sources & evidence
- ORD record
- ord-cae1db8ae628431ca186d6f589031ac1
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04537969
Reaction notes
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