Dimethylformamide dimethyl acetal → HCID 20239749, compound

HRID 1388382Notes

Reaction equation

HRID 1388382 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]1

Participants

6

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10942334Sodium MethoxideHCID 13281192HCID 13281192, compound

Product 1

HCID 20239749HCID 20239749, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the dihydrochloride salt of 4-(4,5-dihydro-1H-imidazol-2-yl)piperidine (0.99 g, 0.0044 M) in methanol (10 ml) which contained sodium methoxide (0.009 M) 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 mixtue of 6-aminopenicillanic acid (0.785 g, 0.0035 M) 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

  1. temperaturerefluxed at 80° C. for 8 hrs
  2. customThe excess of dimethylformamide dimethylacetal was removed

Sources & evidence

ORD record
ord-3c18568edddd46e086c8c849fc39324a
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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