Hydrogen Peroxide → Ketorolac methyl ester

HRID 53903

반응식

HRID 53903 반응식
[CH3:1][O:2][C:3](=[O:21])[CH:4](I)[CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.OO.CCCCCC.C(OCC)(=O)C>CS(C)=O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].S([O-])([O-])(=O)=O.[Fe+2].O>[CH3:1][O:2][C:3]([CH:4]1[C:11]2=[CH:10][CH:9]=[C:8]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:19])[N:7]2[CH2:6][CH2:5]1)=[O:21]

참가 물질

9

반응물 4

HCID 784Hydrogen Peroxide2회HCID 8058HexaneHCID 8857Ethyl AcetateHCID 540699414-(2-Benzoylpyrrol-1-yl)-2-iodobutyric acid methyl ester

생성물 1

HCID 9921553Ketorolac methyl ester

시약·촉매·용매 4

HCID 24393Ferrous Sulfate촉매HCID 62662Ferrous sulfate heptahydrate촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

4-(2-Benzoylpyrrol-1-yl)-2-iodobutyric acid methyl ester (IV, 3.17 grams, 8 mmol) was dissolved in dimethylsulfoxide (32 mL). Iron (II) sulfate heptahydrate (230 mg, 0.827 mmol) was added, and the mixture was stirred for 5 minutes. Hydrogen peroxide (30% aqueous solution, 6 mL) was added dropwise while the internal temperature of the reaction was kept below 35° C. by application of an external water bath. After 45 minutes, TLC (4:1 hexane:ethyl acetate, silica) indicated the reaction was about 60% complete. Additional hydrogen peroxide (2 mL) was added. After 20 minutes more, an additional 2 mL of peroxide and 70 mg of iron sulfate were added) and 15 minutes later, an additional 0.5 mL of peroxide. 20 Minutes after the final peroxide addition, the mixture was poured into water (200 mL). The resulting mixture was extracted with ether (50 mL), then saturated with sodium chloride and extracted twice more with ether. The combined organic extracts were washed twice with water (50 mL each), then once with brine (25 mL), dried over magnesium sulfate, and evaporated in vacuo to afford ketorolac methyl ester (2.095 g, still containing traces of ether (1%) and DMSO (<0.3%) by NMR. Yield calculated on the basis of weight and NMR purity is 96%. The product may be crystallized from methanol, m.p. 80°-82° C.

후처리

  1. customwas kept below 35° C. by application of an external water bath
  2. waitAfter 45 minutes
  3. waitAfter 20 minutes more
  4. extractionThe resulting mixture was extracted with ether (50 mL)
  5. extractionsaturated with sodium chloride and extracted twice more with ether
  6. washThe combined organic extracts were washed twice with water (50 mL each)
  7. dry with materialonce with brine (25 mL), dried over magnesium sulfate
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d2e1d505b8404994853be5a3383ad696
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621115

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