HCID 66990525, compound → HCID 58508551, compound

HRID 454687Notes

Reaction equation

HRID 454687 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]([CH2:43][CH2:44][CH2:45][OH:46])[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>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]([CH2:43][CH2:44][CH2:45][OH:46])[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

5

Reactant 1

HCID 66990525HCID 66990525, compound

Product 1

HCID 58508551HCID 58508551, compoundYield 35.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained methyl 2-(2-(benzyloxy)-5-(2-(4-(3-hydroxypropyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.036 g) in ethyl acetate (1.5 mL) and methanol (1.5 mL), 10% palladium-carbon (0.018 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 hours. To the reaction mixture, 10% palladium-carbon (0.018 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. The insoluble substance was removed by filtration, and then 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: 100-90% chloroform/methanol] to obtain 0.011 g of methyl 2-(2-hydroxy-5-(2-(4-(3-hydroxypropyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 3 hours
  3. customThe insoluble substance was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-c637a71a989f4905a6af921574c14751
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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