p-Toluenesulfonyl azide → 3-azido-N-(tert-butyl)-5-chlorothiophene-2-sulfonamide

HRID 601296

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HRID 601296 반응식
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:14])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]C(CC)C.S([N:30]=[N+:31]=[N-:32])(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[N:30]([C:13]1[CH:12]=[C:11]([Cl:14])[S:10][C:9]=1[S:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:8])=[N+:31]=[N-:32]

참가 물질

5

반응물 3

HCID 13661p-Toluenesulfonyl azideHCID 101063235-Chlorothiophene-2-sulfonic acid tert-butylamideHCID 178418400CID 53628100

생성물 1

HCID 586938313-azido-N-(tert-butyl)-5-chlorothiophene-2-sulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-20 °C

실험 절차

A solution of Example 311A (1.01 g, 3.99 mmol) in tetrahydrofuran (32 mL) at −78° C. was treated with dropwise addition of sec-BuLi (1.4 M in hexane, 2.1 equivalents). The reaction was warmed to −20° C. and stirred for 30 minutes, treated with a solution of tosyl azide (1.1 equivalent) in tetrahydrofuran (7 mL) at −20° C., stirred at 25° C. for 18 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with a gradient of 30% dichloromethane in hexane to 100% dichloromethane to give approximately a 2:1 mixture of starting material to the title compound.

후처리

  1. stirringstirred at 25° C. for 18 hours
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with a gradient of 30% dichloromethane in hexane to 100% dichloromethane
  10. customto give approximately

출처 및 근거

ORD 기록
ord-7efb5ee33b4c451987074e00ee74054e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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