Trifluoromethanesulfonic anhydride → HCID 89350907、化合物

HRID 1470513ノート

反応式

HRID 1470513 の反応式
[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]

参加物

5

反応物 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803、化合物

生成物 1

HCID 89350907HCID 89350907、化合物収率 47%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c1cf468b6ce447bebd7c23c3d985c27e
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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