Water → di-tert-butyl (4-{(3R,4S,5S)-4-amino-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)imidodicarbonate

HRID 924519노트

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HRID 924519 반응식
[N:1]([C@H:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][C@H:5]1[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[N+]=[N-].O.CP(C)C>C1COCC1>[NH2:1][C@H:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:6][C@H:5]1[NH:32][C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34]

참가 물질

5

반응물 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86705280tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate

생성물 1

HCID 86726960di-tert-butyl (4-{(3R,4S,5S)-4-amino-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)imidodicarbonate수율 105%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of di-tert-butyl (4-{(3R,4S,5S)-4-azido-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)imidodicarbonate (1.337 g, 2.441 mmol) in THF (20 mL), water (1.00 mL, 55.5 mmol) was added, followed by trimethylphosphine (383 mg, 5.03 mmol). The mixture was stirred at 50° C. for 15 h. The mixture was then concentrated under reduced pressure. The residue was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the sub-title compound as a white foamy solid (1.336 g, 105%). LCMS calc. for C26H44N5O6 (M+H)+: m/z=522.3. Found: 522.3.

후처리

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e3e54d8bf48346cb9a7316ac89e6ebbb
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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