Water → Methyl [3-(4-chlorophenyl)-4-(2-oxoethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660900
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][CH:12]=C)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:6]1.O.I([O-])(=O)(=O)=[O:24].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][CH:12]=[O:24])[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:6]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 23667635Sodium periodateHCID 58012233Methyl [3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Produkt 1

HCID 58011652Methyl [3-(4-chlorophenyl)-4-(2-oxoethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.00 g (3.25 mmol) of the compound from Example 214A and 217 mg of OsEnCat 40 (micro-encapsulated osmium tetroxide, 0.3 mmol/g, 65 μmol) are placed in 20 ml dioxan and 9 ml water and slowly treated with 2.09 g (9.8 mmol) of sodium periodate at RT. This is allowed to react with vigorous stirring (1-4 days) until HPLC testing of the mixture shows adequate conversion. For the workup, the osmium catalyst is removed by filtration, then washed with dioxan and the total filtrate freed from the organic solvents on the rotary evaporator. The aqueous residue is diluted with more water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and the solvent removed on the rotary evaporator. The oily residue is dried under high vacuum. 948 mg (purity ca. 84%, 79% of theory) of the title compound are obtained.

Aufarbeitung

  1. customto react
  2. customFor the workup, the osmium catalyst is removed by filtration
  3. washwashed with dioxan
  4. customthe total filtrate freed from the organic solvents on the rotary evaporator
  5. additionThe aqueous residue is diluted with more water
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organic phases are dried over sodium sulphate
  8. customthe solvent removed on the rotary evaporator
  9. customThe oily residue is dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b3e4748cc2264bf4bfa54ac24f276b67
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084481B2

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