Triethylamine → 4-[4-(Hydroxyaminocarbonyl)methoxy-3,5-dimethyphenyl]-2-methyl-1(2H)phthalazinone

HRID 1953812노트

반응식

HRID 1953812 반응식
[C:1]([CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([CH3:24])[N:14]=2)=[CH:8][C:7]=1[CH3:25])(O)=[O:2].C(N(CC)CC)C.ClC(OC(C)=C)=O.[Si]([O:47][NH2:48])(C(C)(C)C)(C)C>ClCCl>[OH:47][NH:48][C:1]([CH2:4][O:5][C:6]1[C:7]([CH3:25])=[CH:8][C:9]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([CH3:24])[N:14]=2)=[CH:10][C:11]=1[CH3:12])=[O:2]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 93846Isopropenyl chloroformateHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 700083854-[4-(Carboxy)methoxy-3,5-dimethyphenyl]-2-methyl-1(2H)phthalazinone

생성물 1

HCID 179185964-[4-(Hydroxyaminocarbonyl)methoxy-3,5-dimethyphenyl]-2-methyl-1(2H)phthalazinone수율 8.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of example 108 (1.15 g) in dichloromethane (30 ml) at 0° C. was treated with triethylamine (0.52 g) followed by isopropenyl chloroformate (0.41 g), and the mixture was stirred for 1 h. O-tert-butyldimethylsilylhydroxylamine (0.50 g) was then added and the mixture was stirred for a further 18 h. The reaction mixture was washed with 10% citric acid (20 ml), saturated sodium bicarbonate (20 ml) and the concentrated to dryness in vacuo. A solution of the residual solid in tetrahydrofuran (30 ml) and water (5 ml) was then treated with a 1.0 M solution of tetrabutylammonium fluoride in tetahydrofuran (1 ml) and stirred 1 h the resultant crude mixture was concentrated on to silica and purified by chromatography, eluting with 5% methanol in dichloromethane, to provide the title compound as a white solid (0.10 g).

후처리

  1. stirringthe mixture was stirred for a further 18 h
  2. washThe reaction mixture was washed with 10% citric acid (20 ml), saturated sodium bicarbonate (20 ml)
  3. concentrationthe concentrated to dryness in vacuo
  4. additionA solution of the residual solid in tetrahydrofuran (30 ml) and water (5 ml) was then treated with a 1.0 M solution of tetrabutylammonium fluoride in tetahydrofuran (1 ml)
  5. stirringstirred 1 h the resultant crude mixture
  6. concentrationwas concentrated on to silica
  7. custompurified by chromatography
  8. washeluting with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-a7fad0d52b764d34b4897ee33808c147
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06118001

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