HCID 15671170, compound → HCID 15671171, compound

HRID 2351509Notes

Reaction equation

HRID 2351509 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:32]=[CH:31][C:12]([O:13][CH2:14][C:15]3([CH3:30])[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1>C(O)(=O)C.[Pd]>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:32]=[CH:31][C:12]([O:13][CH2:14][C:15]3([CH3:30])[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1

Participants

4

Reactant 1

HCID 15671170HCID 15671170, compound

Product 1

HCID 15671171HCID 15671171, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.1 g of ethyl 2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-2-methyl-2H-chromene-6-carboxylate (prepared as described in Example 16) were dissolved in 20 ml of acetic acid and hydrogenated for 20 hours under atmospheric pressure at 80° C. in the presence of 2 g of 10% w/w palladium-on-carbon. The catalyst was then removed by filtration, and the filtrate was freed from the solvent by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to afford 1.17 g of the title compound as a white powder.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate was freed from the solvent by evaporation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel
  4. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-7dbfe11bfbed4fb28f280501c19e5437
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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