Chloroform → HCID 58508891, compound

HRID 454682Notes

Reaction equation

HRID 454682 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:34][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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.C(Cl)(Cl)Cl>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:37]=[CH:36][C:35]([N:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)=[CH:34][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12]

Participants

6

Reactant 2

HCID 6212ChloroformHCID 66990348HCID 66990348, compound

Product 1

HCID 58508891HCID 58508891, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-phenoxybenzoate (0.093 g) in ethyl acetate (1.5 mL) and methanol (1.5 mL), 10% palladium-carbon (0.047 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. Chloroform was added to the reaction mixture. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 80-70% hexane/ethyl acetate] to obtain 0.067 g of tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-phenoxybenzoate 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. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 80-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-43d58093b9e745efb2d4db9be0060b48
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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