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

HRID 2046397ノート

反応式

HRID 2046397 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-06c002f508c44fbfad1dec3206fe19a1
出典データセット
uspto-grants-2013_11
特許番号
US08592425B2

反応ノート

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