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

HRID 660900노트

반응식

HRID 660900 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3e4748cc2264bf4bfa54ac24f276b67
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084481B2

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