HCID 86649116, compound → HCID 67381735, compound

HRID 1471027Notes

Reaction equation

HRID 1471027 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:25]2[CH:40]=[CH:39][C:28]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[C:27]([N+:41]([O-])=O)[CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.C1COCC1.[Pt](=O)=O>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]2[N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)[CH:12]([C:25]3[CH:26]=[C:27]([NH2:41])[C:28]([NH:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=4)=[CH:39][CH:40]=3)[CH2:13][CH2:14]2)=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 86649116HCID 86649116, compound

Product 1

HCID 67381735HCID 67381735, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 179D (2.74 g, 4.72 mmol) in EtOH (25 mL) and THF (25 mL) was added platinum(IV) oxide (0.5 g, 2.2 mmol). The resulting mixture was stirred at rt under 1 atm H2 overnight. The mixture was filtered through celite, washed with methanol, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-45% EtOAc in hexane to give the title compound (1.74 g, 71%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-45% EtOAc in hexane

Sources & evidence

ORD record
ord-7f755ed8b6b045e19bd5cb7abbcf1b3d
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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