HCID 66886387, compound → HCID 66884887, compound

HRID 76863Notes

Reaction equation

HRID 76863 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]=[C:6]([C:8]1[N:9]=[CH:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1)[CH3:7])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]([C:8]1[N:9]=[CH:10][N:11]([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=1)[CH3:7])[CH3:2]

Participants

4

Reactant 1

HCID 66886387HCID 66886387, compound

Product 1

HCID 66884887HCID 66884887, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of 3-(1-trityl-1H-imidazol-4-yl)but-2-enoic acid ethyl ester (5 g, 11.8 mmol) in ethanol (100 mL) in a Parr bottle is added 5% palladium on carbon (0.5 g). The bottle is purged with nitrogen, evacuated, and hydrogen gas (15 psi) added. The bottle is placed upon a Parr hydrogenation apparatus and shaken for 18 h. The hydrogen is evacuated and the bottle purged with nitrogen gas. The reaction mixture is then filtered through diatomaceous earth and the clear liquid solution collected and the solvent removed in vacuo to give the crude oil, which is subject to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound.

Workup

  1. customThe bottle is purged with nitrogen
  2. customevacuated
  3. additionhydrogen gas (15 psi) added
  4. customThe hydrogen is evacuated
  5. customthe bottle purged with nitrogen gas
  6. filtrationThe reaction mixture is then filtered through diatomaceous earth
  7. customthe clear liquid solution collected
  8. customthe solvent removed in vacuo
  9. customto give the crude oil, which
  10. washeluting with MeOH

Sources & evidence

ORD record
ord-4daf185d7f484fc5a801abdbf3f0f4f1
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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