HCID 66990288, compound → HCID 58508925, compound

HRID 454617Notes

Reaction equation

HRID 454617 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:46][CH2:45][C:40]3([O:44][CH2:43][CH2:42][O:41]3)[CH2:39][CH2:38]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[O:41]1[C:40]2([CH2:39][CH2:38][N:37]([C:34]3[CH:35]=[CH:36][C:9]([OH:8])=[C:10]([CH:33]=3)[C:11]([NH:13][C:14]3[CH:26]=[C:25]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:24]=[CH:23][C:15]=3[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[O:12])[CH2:46][CH2:45]2)[O:44][CH2:43][CH2:42]1

Participants

5

Reactant 1

HCID 66990288HCID 66990288, compound

Product 1

HCID 58508925HCID 58508925, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)benzamido)-4-phenylbenzoate (0.18 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.091 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. Ethyl acetate was added to the reaction mixture. The insoluble substance was removed by filtration, and then 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 0.12 g of tert-butyl 2-(5-(1,4-dioxa-8-azaspiro[4,5]decan-8-yl)-2-hydroxybenzamido)-4-phenylbenzoate as a 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-45885c327cf34ba093d61e2b2dcdb69e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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