Sodium Azide → tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate

HRID 924503노트

반응식

HRID 924503 반응식
CS(O[C@@H:6]1[C@@H:11]([CH3:12])[CH2:10][N:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C@H:7]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])(=O)=O.[N-:42]=[N+:43]=[N-:44].[Na+]>CN(C=O)C>[N:42]([C@H:6]1[C@@H:11]([CH3:12])[CH2:10][N:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:19]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:8][C@H:7]1[NH:34][C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])=[N+:43]=[N-:44]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86705229(3R,4R,5S)-1-(3-(bis(tert-butoxycarbonyl)amino)pyridin-4-yl)-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-4-yl methanesulfonate

생성물 1

HCID 86705280tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of (3R,4R,5S)-1-{3-[bis(tert-butoxycarbonyl)amino]pyridin-4-yl}-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-4-yl methanesulfonate (0.57 g, 0.96 mmol) in DMF (5.0 mL), sodium azide (0.31 g, 4.8 mmol) was added. The reaction mixture was heated at 90° C. for 5 h then allowed to cool. The solution was then partitioned between EtOAc and water. The layers were separated organic layer was washed with aq. Na2CO3 and brine, then dried, filtered and concentrated under reduced pressure to give the sub-title compound (0.52 g, 99%). LCMS calc. for C26H42N7O6 (M+H)+: m/z=548.3. Found: 548.4.

후처리

  1. temperatureto cool
  2. customThe solution was then partitioned between EtOAc and water
  3. customThe layers were separated organic layer
  4. washwas washed with aq. Na2CO3 and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e87f659162f14e8081f76d24ee65b023
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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