Ethanol → HCID 67236803, compound

HRID 2364794Notes

Reaction equation

HRID 2364794 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:11][CH2:10][C@@H:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.C(O)C>O=[Pt]=O.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH2:11][CH2:10][C@@H:9]2[C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 86649104HCID 86649104, compound

Product 1

HCID 67236803HCID 67236803, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 38B (2.34 g, 5.74 mmol) in 1:1 ethanol:THF (60 ml) in a 250 mL stainless steel pressure bottle was added PtO2 (0.47 g, 2.06 mmol) and the resulting mixture was placed under H2 pressure (30 psi) and stirred at rt. for 90 min. The mixture was filtered through a nylon membrane and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-65% ethyl acetate in hexanes to give the title compound as a solid (0.736 g, 37%).

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-65% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c7b22add9d3746cc9b1ae4c018c526e5
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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