Dimethylformamide dimethyl acetal → HCID 20239797, compound

HRID 1388407Notes

Reaction equation

HRID 1388407 reaction equation
[N:1]1([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:13][O:14][CH:15]([O:19][CH3:20])N(C)C>>[CH3:13][O:14][CH:15]([O:19][CH3:20])[N:10]1[CH2:11][CH2:12][CH:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 226629174-[(1H-Imidazol-1-yl)methyl]piperidine

Product 1

HCID 20239797HCID 20239797, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[(1H-imidazol-1-yl)methyl]-piperidine (5 g, 0.03 M) and dimethylformamide dimethylacetal (40 ml) was heated at 100° C. for 8 hrs. Removal of the excess of dimethylformamide dimethylacetal gave 4-[(imidazol-1-yl)methyl]-1-piperidine carboxaldehyde dimethylacetal (6.33 g) which was dissolved in methylene chloride (25 ml) and added to the mixture of 6-aminopenicillanic acid (5.15 g, 0.024 M) and diisopropylethylamine (3.14 ml) in methylene chloride (90 ml) at 0° C. The reaction was stirred at 0° C. for 1 hr and room temperature for 3 hrs. The solvent was then removed and water (80 ml) was added. After being washed with ethylacetate, the aqueous solution, acidified to pH 3, was purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta)]-6-[[[4-(1H-imidazol-1-yl-methyl)-1-piperidinyl]methylene]amino]-3,3 -dimethyl-6-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (5.2 g, 55% yield).

Workup

  1. customRemoval of the excess of dimethylformamide dimethylacetal

Sources & evidence

ORD record
ord-44bfc3e90f15428aa9bea30a2ca82049
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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