Chloroform → HCID 58508604, compound

HRID 454706Notes

Reaction equation

HRID 454706 reaction equation
C([O:8][C:9]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[O:28][CH:29]=[CH:30][CH:31]=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>CO.C(OCC)(=O)C.[C].[Pd]>[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[C:25]1[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:32]=[C:33]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:34]=[CH:35][C:9]=2[OH:8])[CH:26]=1

Participants

6

Reactant 2

HCID 6212ChloroformHCID 66990168HCID 66990168, compound

Product 1

HCID 58508604HCID 58508604, compoundYield 72.5%

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-(morpholin-4-yl)benzamido)-4-(furan-2-yl)benzoate (0.14 g) in methanol (2.0 mL) and ethyl acetate (2.0 mL), 10% palladium-carbon (0.029 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. 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: 85-75% hexane/ethyl acetate] to obtain 0.085 g of tert-butyl 4-(furan-2-yl)-2-(2-hydroxy-5-(morpholin-4-yl)benzamido)benzoate 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: 85-75% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-d9383bec3b6440148155131ab55487cb
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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