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

HRID 1895880노트

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HRID 1895880 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>[N:25]([C@H:7]1[C:8]([F:22])([F:21])[CH2:9][CH2:10][CH2:11][C@H:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N+:26]=[N-:27]

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]carbamate수율 56.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A solution of (1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate 26 (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 (0-15% ethyl acetate in hexanes) gave 0.94 g (56%) of tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate 28 as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.75 (1H, m), 3.98 (1H, bs), 3.88 (1H, bm), 1.96 (2H, m), 1.70 (2H, m), 1.46 (9H, s), 1.37 (2H, m).

후처리

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washThe organics were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by flash chromatography (0-15% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5313a8c1b9954d059a711e5c03768d31
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518911B2

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