Trifluoromethanesulfonic anhydride → HCID 89350907, 화합물

HRID 1470513노트

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HRID 1470513 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=[C:7]2[O:15]C.C[CH2:18][N:19]([CH:23](C)C)C(C)C.[O:26](S(C(F)(F)F)(=O)=O)[S:27]([C:30]([F:33])([F:32])[F:31])(=O)=[O:28]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[S:27]([O:15][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[C:10]([C:12](=[O:13])[N:19]([CH3:23])[CH3:18])=[CH:9][CH:8]=1)(=[O:28])=[O:26]

참가 물질

5

반응물 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803, 화합물

생성물 1

HCID 89350907HCID 89350907, 화합물수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-6 intermediate) (0.14 g, 0.561 mmol) in DCM (5 mL) was added, DIPEA (0.20 mL, 1.12 mmol) at 0° C. After 5 min stirring, Tf2O (0.11 mL, 0.67 mmol) was added to it. The resulting mixture was stirred for 2 h before quenching with ice water. The aqueous layer was extracted with DCM, and the combined organic layer was washed with, water, brine, dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography to furnish the desired trifliate intermediate as a pale yellow oil (100 mg, 47%).

후처리

  1. additionwas added
  2. customat 0° C
  3. stirringThe resulting mixture was stirred for 2 h
  4. custombefore quenching with ice water
  5. extractionThe aqueous layer was extracted with DCM
  6. washthe combined organic layer was washed with, water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c1cf468b6ce447bebd7c23c3d985c27e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006442B2

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