HCID 57834999, compound → HCID 57834986, compound

HRID 730589Notes

Reaction equation

HRID 730589 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([C:17]3[CH:21]=[CH:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:18]=3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([CH:17]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:9]1=[O:36])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 57834999HCID 57834999, compound

Product 1

HCID 57834986HCID 57834986, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a Parr vessel flushed with nitrogen was added a 5% dispersion of platinum on charcoal (15 mg) followed by a solution of 3-benzyl-7-(1-tert-butoxycarbonyl-1H-pyrrol-3-yl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (0.150 g., 0.307 mmol) in 10 mL methanol. The Parr vessel was vacuum-purged with hydrogen at atmospheric pressure and stirred for 95 hours. The reaction mixture was then vacuum-purged with nitrogen, filtered through a plug of celite to remove catalyst, and concentrated in vacuo. The resulting residue was purified by flash chromatography (5 to 10% gradient ethyl acetate in hexanes) to give 80 mg of racemic 3-benzyl-7-(1-tert-butoxycarbonyl-pyrrolidin-3-yl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester as a clear oil. MS: 516 (M+Na)+.

Workup

  1. customTo a Parr vessel flushed with nitrogen
  2. additionwas added a 5% dispersion of platinum on charcoal (15 mg)
  3. customThe Parr vessel was vacuum-purged with hydrogen at atmospheric pressure
  4. customThe reaction mixture was then vacuum-purged with nitrogen
  5. filtrationfiltered through a plug of celite
  6. customto remove catalyst
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by flash chromatography (5 to 10% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7de6db2495ee44b88bcdbf8fc01ff890
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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