Sodium Azide → tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate

HRID 2046397노트

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HRID 2046397 반응식
FC(F)(F)S(O[C@H:7]1[C@H:12]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][CH2:9][C:8]1([F:22])[F:21])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[C:17]([O:16][C:14](=[O:15])[NH:13][C@@H:12]1[CH2:11][CH2:10][CH2:9][C:8]([F:22])([F:21])[C@@H:7]1[N:25]=[N+:26]=[N-:27])([CH3:20])([CH3:19])[CH3:18]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 58046391(1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate

생성물 1

HCID 58046406tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

is A solution of (1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate (2.32 g, 6.05 mmol) and sodium azide (2.36 g, 36.3 mmol) in DMF was sealed and heated to 100° C. for 3 hours in a microwave reactor. The reaction was partitioned between water and ethyl acetate. The organics were washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography afforded the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.75 (m, 1H); 3.98 (br s, 1H); 3.88 (m, 1H); 1.96 (m, 2H); 1.70 (m, 2H); 1.46 (s, 9H); 1.37 (m, 2H). tert-Butyl[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate was also obtained from this procedure: 1H NMR (500 MHz, CDCl3) 4.82-4.80 (d, 1H); 3.93-3.89 (dt, 1H); 3.31-3.27 (m, 1H); 2.24-2.19 (m, 1H); 2.13-2.10 (m, 1H); 1.86-1.67 (m, 2H); 1.55-1.52 (m, 2H); 1.48-1.41 (m, 11H). 19F NMR (CDCl3, 564 MHz) −102.2-−102.7 (d, 1F); −113.9-−114.5 (m, 1F).

후처리

  1. customwas sealed
  2. customThe reaction was partitioned between water and ethyl acetate
  3. washThe organics were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-06c002f508c44fbfad1dec3206fe19a1
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592425B2

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