Dimethylformamide dimethyl acetal → HCID 20239793, compound

HRID 364740Notes

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[C:15]([OH:17])=[O:16])[CH2:3][CH2:2]1.C[O-].[Na+].[CH3:21][O:22]C(OC)N(C)C>CO>[C:15]([C:11]1[N:10]([CH2:9][CH2:8][CH2:7][CH:4]2[CH2:5][CH2:6][N:1]([CH:21]=[O:22])[CH2:2][CH2:3]2)[CH:14]=[CH:13][N:12]=1)([OH:17])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[3-(4-piperidinyl)propyl]-1H-imidazole-2-carboxylic acid 1.75 molar hydrochloride 0.65 molar hydrate (1.3 g, 0.0047M) and sodium methoxide (0.005M) in methanol (23 ml) was added to dimethylformamide dimethylacetal (15 ml) and heated at 80° C. for 8 hrs. The reaction mixture was filtered and stripped to dryness to give 4-[3-(2-carboxy-1H-imidazol-1-yl)propyl]-1-piperidine carboxaldehyde. The solution of the above piperidine carboxaldehyde dimethylacetal in methanol (5 ml) was then added to a mixture of 6-aminopenicillanic acid (0.81 g, 0.0037M) and diisopropylethylamine (0.4 ml) in chloroform (30 ml) at 0° C. The reaction was stirred at 0° C. 2 hrs and room temperature for 2 hrs. The solvent was removed and water (15 ml) was added. After being washed with ether, the aqueous solution, acidified to pH 3 to about 3.5, was purified on Sephadex LH 20 columns to give [2S-(2alpha,5alpha,6beta]-6-[[[1-(3-(2-carboxy-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 (0.38 g, 17% yield).

Workup

filtrationThe reaction mixture was filtered

Sources & evidence

ORD record: ord-bd1231cd24b04eea8b1dcb05517904e7
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605744

Reaction notes

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