HCID 178418361, compound → HCID 178451915, compound

HRID 2364799Notes

Reaction equation

HRID 2364799 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[N:29]=[C:30]([C@@H:33]4[CH2:37][CH2:36][CH2:35][N:34]4[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[NH:31][CH:32]=3)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[H][H]>C(O)C.C1COCC1.[Pt](=O)=O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:9]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:29]=[C:30]([C@@H:33]5[CH2:37][CH2:36][CH2:35][N:34]5[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[NH:31][CH:32]=4)=[CH:24][CH:23]=3)[CH2:10][CH2:11]2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178451917HCID 178451917, compound

Product 1

HCID 178451915HCID 178451915, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolved the product from Example 39F (300 mg, 0.502 mmol) in ethanol (5 mL) and THF (5 mL) then added platinum(IV) oxide (22.8 mg, 0.1 mmol) and a hydrogen balloon and stirred the solution at room temperature for 2.5 h. Solution was filtered through celite and washed with methanol (10 mL), then concentrated to give the title compound (285 mg, 100%) as a colorless semi-solid and a 1/1 mixture of stereoisomers.

Workup

  1. filtrationSolution was filtered through celite
  2. washwashed with methanol (10 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-366a52228b964452bfbdcebea1d5d9f7
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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