HCID 69946086, compound → HCID 22898674, compound

HRID 1018520Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=2[O:30][CH3:31])[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=2[O:30][CH3:31])=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]([CH3:17])=[N:14][C:15]=1[CH3:16])=[O:9]

Participants

Reactant 2

HCID 69946086HCID 69946086, compound

HCID 178418287HCID 178418287, compound

Product 1

HCID 22898674HCID 22898674, compoundYield 79%

Procedure

A mixture of 11 g (0,025 mol) of 2,6-dimethyl-4-(2,3-dimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester and 92 g (0,076 mol) of pyridinium chlorochromate absorbed on alumina, was suspended on 250 ml of CH2C12, and the whole mixture was maintained on stirring at room temperature for 6 hours. The remaining solid was eliminated by filtration, and the liquid was washed with water (3×300 ml), dried over anh. Na2SO4, and concentrated at reduced pressure, to dryness. The product was obtained as an oil, which was purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 79%.

Workup

customabsorbed on alumina
temperaturethe whole mixture was maintained
filtrationThe remaining solid was eliminated by filtration
washthe liquid was washed with water (3×300 ml)
dry with materialdried over anh. Na2SO4
concentrationconcentrated at reduced pressure, to dryness
customThe product was obtained as an oil, which
customwas purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 79%

Sources & evidence

ORD record: ord-59f564ea173b4e42b900627dba675cd3
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482841B1

Reaction notes

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