반응식
[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:31][CH:32]=[CH2:33])[C:11]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22](=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH:20]([CH3:21])[C:14]2=[N:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CC(C1C=C(C(C)C)C(S([N:60]=[N+:61]=[N-:62])(=O)=O)=C(C(C)C)C=1)C.CC(O)=O>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:31][CH:32]=[CH2:33])[C:11]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22](=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][C@:20]([N:60]=[N+:61]=[N-:62])([CH3:21])[C:14]2=[N:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- -78 °C
실험 절차
To a solution of the methyl diastereomers (18c) (3.90 g, 8.51 mmol) in 40 mL THF at −78° C., was added LiHMDS (IM in THF, 17.9 mL, 17.9 mmol). The red solution was stirred at −78° C. for 5 min, then a solution of trisyl azide (2.90 g, 9.36 mmol) in 8 mL THF was added. The reaction was stirred at −78° C. for 1.5 h, then was quenched with the addition of AcOH (2.19 mL, 38.3 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with 1N HCl, H2O and brine, dried (Na2SO4), and concentrated. The product was purified by flash chromatography (35 to 40% EtOAc/hexanes) to afford 2.764 g (65%) of azide 18d. MS (ESI) 500.4 (M+H+), 522.4 (M+Na+).
후처리
- stirringThe reaction was stirred at −78° C. for 1.5 h
- stirringThe mixture was stirred at rt for 1 h
- washThe organic phase was washed with 1N HCl, H2O and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe product was purified by flash chromatography (35 to 40% EtOAc/hexanes)
출처 및 근거
- ORD 기록
- ord-832d2b39b7bf4896951ab0ab2b27acfd
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07094783B2
연결된 노트
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