Dichloromethane → 2,5-Dihydro-3,6-dimethoxy-2-isopropyl-5-(2'-iodo-4'-hydroxy-5'-formylbenzyl)-(2R,5S)-pyrazine
반응식
B(Cl)(Cl)Cl.ClCCl.COC1C(CC2C=CC=CC=2)=NC=CN=1.[CH3:23][O:24][C:25]1[C@@H:26]([CH:45]([CH3:47])[CH3:46])[N:27]=[C:28]([O:43][CH3:44])[C@H:29]([CH2:31][C:32]2[CH:37]=[C:36]([CH:38]=[O:39])[C:35]([O:40]C)=[CH:34][C:33]=2[I:42])[N:30]=1>>[CH3:23][O:24][C:25]1[C@@H:26]([CH:45]([CH3:47])[CH3:46])[N:27]=[C:28]([O:43][CH3:44])[C@H:29]([CH2:31][C:32]2[CH:37]=[C:36]([CH:38]=[O:39])[C:35]([OH:40])=[CH:34][C:33]=2[I:42])[N:30]=1참가 물질
반응물 4
생성물 1
반응 조건
- 온도
- 0 °C
실험 절차
A 1M solution of BCl3 in dichloromethane (11.8 mL, 11.8 mmol) was added drop wise to a solution of the methoxybenzyl pyrazine analog 22 (134.80 mg, 0.30 mmol) and stirred at 0° C. under argon. The solution changed in color from the initial orange to light brown and finally to greenish brown. The reaction mixture was stirred for one hour at 0° C. and warmed slowly to room temperature over night. The reaction mixture was poured into ice-water and stirred for 15 min. The mixture was extracted with dichloromethane and the organic phase was dried with Na2SO4. Evaporation of the solvent gave a yellow brown oil which upon flash chromatographic purification provided pure 2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2′-iodo-4′-hydroxy-5′-formylbenzyl)-(2R,5S)-pyrazine (24) (41.40 mg, 32%).
후처리
- stirringThe reaction mixture was stirred for one hour at 0° C.
- temperaturewarmed slowly to room temperature over night
- stirringstirred for 15 min
- extractionThe mixture was extracted with dichloromethane
- dry with materialthe organic phase was dried with Na2SO4
- customEvaporation of the solvent
- customgave a yellow brown oil which upon flash
- custompurification
출처 및 근거
- ORD 기록
- ord-7dfe001bc066470aa74f19619728b499
- 출처 데이터셋
- uspto-grants-2014_03
- 특허 번호
- US08674101B2
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