1,2-Dimethoxyethane → Di-tert-butyl{3-[3-(bromomethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate

HRID 1930772노트

반응식

HRID 1930772 반응식
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:26][N:25]=[C:24]([CH2:27]O)[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.COCCOC.P(Br)(Br)[Br:43]>O>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:26][N:25]=[C:24]([CH2:27][Br:43])[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 57867426Di-tert-butyl{3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate

생성물 1

HCID 57867418Di-tert-butyl{3-[3-(bromomethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate수율 15.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of di-tert-butyl{3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate (0.78 g, 2 mmol), triethylamine (1.95 mL, 14 mmol) and 1,2-dimethoxyethane (10 mL) was added phosphorus tribromide (0.37 mL, 4 mmol) dropwise at 0° C., which was stirred at room temperature for two hours, and then stirred at 50° C. for 30 minutes. The reaction mixture was cooled to 0° C., then water was added thereto and extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride water. After drying over anhydrous magnesium sulfate and filtering, the solvent was evaporated under a reduced pressure, the residue was purified by silica gel column chromatography to obtain the title compound (0.14 g).

후처리

  1. stirringstirred at 50° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationfiltering
  7. customthe solvent was evaporated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-05df349dbb894799866e23703ddffd95
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188119B2

반응 노트

불러오는 중…