Perfluoro-1-butanesulfonyl fluoride → HCID 118045501, 화합물

HRID 595966노트

반응식

HRID 595966 반응식
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

참가 물질

6

반응물 4

HCID 67814Perfluoro-1-butanesulfonyl fluoride2회HCID 81531DiisopropylethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 11032835HCID 11032835, 화합물

생성물 1

HCID 118045501HCID 118045501, 화합물수율 30%

시약·촉매·용매 1

HCID 7368(Trifluoromethyl)benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ea4caffecdc04c22826c17e1a1919dbf
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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