HCID 21196490, compound → HCID 21196492, compound

HRID 1067137Notes

Reaction equation

HRID 1067137 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:23][C:24]4[CH:25]=[C:26]([C:30]5[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38][CH3:39])=[O:37])[CH:31]=5)[CH:27]=[CH:28][CH:29]=4)[CH2:20][CH2:21][CH:22]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOC(C)=O.CO.[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[CH2:23][C:24]3[CH:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38][CH3:39])=[O:37])[CH:31]=4)[CH:27]=[CH:28][CH:29]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 21196490HCID 21196490, compound

Product 1

HCID 21196492HCID 21196492, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3′-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl}biphenyl-3-carboxylate (204 mg) and 10% Pd/C (wet) (50 mg) in EtOAc (3 ml) and MeOH (3 ml) was stirred under hydrogen atmosphere at room temperature for 14 hours. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 12:1 to 6:1) to give methyl 3′-{[2-(4,5-diphenyloxazol-2-yl)-1-cyclopentyl]methyl}biphenyl-3-carboxylate (172.1 mg) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 12:1 to 6:1)

Sources & evidence

ORD record
ord-d8ae5de860b443d28c83fdb2e3e0984b
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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