Ethanol → HCID 20745174, compound

HRID 378150Notes

Reaction equation

HRID 378150 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][CH:17]([C:22]2[CH:30]=[CH:29][C:25]3[O:26][CH2:27][O:28][C:24]=3[CH:23]=2)[CH2:18][C:19]([O-:21])=[O:20])=[O:15])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH2:31](O)[CH3:32].[CH2:34]([N:41]=[C:42]=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>[Pd].C(OCC)C>[C:35]1([CH2:34][NH:41][C:42]([NH:1][C:4]2[CH:5]=[C:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][CH:17]([C:22]3[CH:30]=[CH:29][C:25]4[O:26][CH2:27][O:28][C:24]=4[CH:23]=3)[CH2:18][C:19]([O:21][CH2:31][CH3:32])=[O:20])=[O:15])=[O:11])[CH:7]=[CH:8][CH:9]=2)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 76639Benzyl isocyanateHCID 22608562HCID 22608562, compound

Product 1

HCID 20745174HCID 20745174, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

The compound of Example 120 (2 g, 0.62 mmol) was added to absolute ethanol (60 mL) in a Parr jar. Palladium on carbon 5% (500 mg) was added and the mixture was hydrogenated under 50 psi in a Parr apparatus for a period of 1.5 hours. After complete reaction the palladium catalyst was removed by filtration through a plug of celite. The solvent was removed under reduced pressure and the sample dried in vacuo. Acetonitrile (5 mL) was added to the crude aniline followed by benzyl isocyanate (700 mg, 0.75 mmol). The solution turned to a solid. Diethyl ether was added and the product filtered. The product was purified by reverse phase chromatography (water/acetonitrile) and lyophilized to result in a white solid (1.5 g). MS and 1H-NMR were consistent with the proposed structure.

Workup

  1. customwas removed by filtration through a plug of celite
  2. customThe solvent was removed under reduced pressure
  3. customthe sample dried in vacuo
  4. additionAcetonitrile (5 mL) was added to the crude aniline
  5. filtrationthe product filtered
  6. customThe product was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-1f2b83b286e34a1a97b568f7f9597555
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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