1,4-Dioxane → HCID 58508919, compound

HRID 454693Notes

Reaction equation

HRID 454693 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][N:40]([S:43]([CH3:46])(=[O:45])=[O:44])[CH2:39][CH2:38]2)=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12])C1C=CC=CC=1.O1CCOCC1>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]2[CH2:38][CH2:39][N:40]([S:43]([CH3:46])(=[O:45])=[O:44])[CH2:41][CH2:42]2)=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12]

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 66991255HCID 66991255, compound

Product 1

HCID 58508919HCID 58508919, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained methyl 2-(2-(benzyloxy)-5-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.085 g) in ethyl acetate (3.0 mL), methanol (1.5 mL), and dioxane (6.0 mL), 10% palladium-carbon (0.085 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.063 g of methyl 2-(2-hydroxy-5-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. additionwas added
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-ed06af3f1f684ddc88ffda56ac787687
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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