Sodium Carbonate → (11S)-11-Isopropyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline 5-oxide

HRID 1035493노트

반응식

HRID 1035493 반응식
[CH:1]([C@@H:4]1[N:9]2[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[CH:12][C:11]=3[N:20]=[C:8]2[CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:26].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH:1]([C@@H:4]1[N:9]2[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N+:13]([O-:26])=[CH:12][C:11]=3[N:20]=[C:8]2[CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67157166(11S)-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

생성물 1

HCID 67156776(11S)-11-Isopropyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline 5-oxide수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(11S)-11-Isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (1.13 g, 4.23 mmol) was dissolved in 40 mL of CH2Cl2 and treated with 3-chloroperoxybenzoic acid (MCPBA) (1.13 g, 77% max). After stirring for 75 minutes, the reaction was treated with 20 mL of 2% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with 10 mL of brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give (11S)-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (1.20 g) as a crusty, off-white solid.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic layers were washed with 10 mL of brine
  4. dry with materialThe organic portion was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-74922e7a2ad74dd0ae6b34547796e24a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546383B2

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