Perfluoro-1-butanesulfonyl fluoride → HCID 118045501、化合物

HRID 595966ノート

反応式

HRID 595966 の反応式
O[CH2:2][C@@H:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F.F.F.C(N(CC)CC)C.[F:31]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.CCN(C(C)C)C(C)C>C1(C(F)(F)F)C=CC=CC=1>[F:31][CH2:2][C@@H:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 67814Perfluoro-1-butanesulfonyl fluoride2 回HCID 81531DiisopropylethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 11032835HCID 11032835、化合物

生成物 1

HCID 118045501HCID 118045501、化合物収率 30%

試薬・触媒・溶媒 1

HCID 7368(Trifluoromethyl)benzene溶媒

実験手順

To a solution of (S)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.5 g, 5.61 mmol) in PhCF3 (18.71 mL) was added triethylamine trihydrofluoride (5.48 mL, 33.7 mmol), perfluorobutanesulfonyl fluoride (1.019 mL, 5.67 mmol), DIEA (14.70 mL, 84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h, then more perfluorobutanesulfonyl fluoride (1.019 mL, 5.67 mmol) was added. After 5 h, the reaction mixture was quenched with NaHCO3 and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% EtOAC in heptane) yielding (S)-2-(2-fluoro-1-phenylethyl)isoindoline-1,3-dione (30% yield). LCMS (m/z): 270.1 (MH+), 0.96 min.

後処理

  1. waitAfter 5 h
  2. customthe reaction mixture was quenched with NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (0-10% EtOAC in heptane)

出典と根拠

ORDレコード
ord-ea4caffecdc04c22826c17e1a1919dbf
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

読み込み中…