HCID 21458485, compound → HCID 21458482, compound

HRID 725249Notes

Reaction equation

HRID 725249 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][C:7]=1[N+:28]([O-])=O)=[O:4].[H][H]>CN(C)C=O.[Pt](=O)=O>[NH2:28][C:7]1[CH:8]=[C:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:31])([CH3:1])[CH3:32]

Participants

5

Reactant 2

HCID 21458485HCID 21458485, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21458482HCID 21458482, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under nitrogen, the title compound of Example 28A (15.77 g, 35.0 mmol) was dissolved in 350 ml dimethylformamide. 500 mg platinum (IV) oxide were added, the mixture was heated to 60° C. and hydrogenated by monitoring with thin layer chromatography until the end of the reaction (1-5 days). The hydrogen was replaced with nitrogen, the catalyst was filtered off and the filtrate evaporated (all operations under nitrogen, otherwise the product has a deep blue color). The residue was triturated with degassed water to remove residual dimethylformamide. Yield after drying of title compound: 14.1 g (96%) m.p. 115° C.

Workup

  1. customhydrogenated by monitoring with thin layer chromatography until the end of the reaction (1-5 days)
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate evaporated (all operations under nitrogen
  4. customThe residue was triturated with degassed water
  5. customto remove residual dimethylformamide
  6. customYield
  7. dry with materialafter drying of title compound

Sources & evidence

ORD record
ord-773420a2f1df4a86bdbf48da827fd4c3
Source dataset
uspto-grants-1998_01
Patent number
US05705645

Reaction notes

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