Tetrabutylammonium Fluoride → (S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879264노트

반응식

HRID 879264 반응식
[Br:1][C:2]1[S:3][C:4]2[C:10]([O:11]S(C(F)(F)F)(=O)=O)=[C:9]([C@H:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=2[N:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[S:3][C:4]2[C:10]([OH:11])=[C:9]([C@H:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=2[N:6]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86699785(S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate

생성물 1

HCID 71003373(S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate (32): (500 mg, 0.938 mmol) in THF (5 mL) was added TBAF (1.0 M in THF, 4 mL) slowly. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was washed by a mixture of H2O (20 mL) and HOAc (200 ul), extracted by EtOAc, the organic phase was washed by sat. NaHCO3, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-40% EtOAc in hexanes to give 75A (380 mg). LCMS-ESI+: calc'd for C16H20BrNO4S: 402.0 (M+H+); Found: 401.9 (M+H+).

후처리

  1. washThe reaction mixture was washed by a mixture of H2O (20 mL) and HOAc (200 ul)
  2. extractionextracted by EtOAc
  3. washthe organic phase was washed by sat. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-40% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-ca05d1f11c854cdb9cef37fc7e47cd5b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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