Dimethylformamide dimethyl acetal → HCID 131713387, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[NH2:15])[CH2:3][CH2:2]1.[CH3:16][O:17][CH:18]([O:22][CH3:23])N(C)C>>[CH3:23][O:22][CH:18]([O:17][CH3:16])[N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[N:15]=[CH:9][N:10]([CH3:14])[CH3:11])[CH2:3][CH2:2]1Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-[3(4-piperidinyl)propyl]-1H-imidazole-2-amine (0.5 g, 0.0024M) and dimethylformamide dimethylacetal (7 ml) was heated at 100° C. for 10 hrs. The reaction was then stripped to dryness to give 4-[3-(2[[[dimethylamino)methylene]amino]-1H-imidazol-1-yl]propyl]-1-piperidinecarboxaldehyde dimethylacetal. The solution of the piperidinecarboxaldehyde dimethylacetal in chloroform (4 ml) was added to the mixture of 6-aminopenicillanic acid (0.46 g, 0.0216M) and diisopropylethylamine (0.37 ml) in chloroform (10 ml) at 0° C. and then stirred at room temperature for 31/2 hrs. After this period, the solvent was removed and water (20 ml) was added. The aqueous solution, after being washed with ethylacetate, was acidified from about pH 3 to about 3.5 and purified on Sephadex L-20 columns to give [2S-(2alpha,5alpha,6beta)]-6-[[[4-[3 -[2-[[(dimethylamino)methylene]amino]-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 1.7 molar hydrochloride 2.6 molar hydrate (0.64 g, 64% yield).
Sources & evidence
- ORD record
- ord-6ab43fb6e00c4d71a3411604fa71c649
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04605744
Reaction notes
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