N-(Diphenylmethylene)glycine tert-butyl ester → Tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate

HRID 2369523노트

반응식

HRID 2369523 반응식
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.FC(F)(F)S(O[CH2:57][CH2:58][C:59]([F:62])([F:61])[F:60])(=O)=O>C1COCC1>[C:1]1([C:7](=[N:14][CH:15]([CH2:57][CH2:58][C:59]([F:62])([F:61])[F:60])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 141328493,3,3-Trifluoropropyl trifluoromethanesulfonateHCID 22742125Tetrahydrofuran heptane ethylbenzol

생성물 1

HCID 86695928Tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of tert-butyl 2-((diphenylmethylene)amino)acetate (1 g, 3.39 mmol) in THF (20 ml) cooled to −78° C. under nitrogen atmosphere was added LDA, 2M in THF/heptane/ethylbenzene (2.54 ml, 5.08 mmol) dropwise for 30 mins. To this mixture was then added 3,3,3-trifluoropropyl trifluoromethanesulfonate (1.083 g, 4.40 mmol). The reaction was gradually warmed to rt and stirred for 4 h. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride at 0° C. The reaction mixture was then extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 2% ethyl acetate in hexane to afford tert-butyl 2-((diphenylmethylene)amino)-5,5,5-trifluoropentanoate (800 mg, 2.02 mmol, 60% yield) as a yellow oil. LCMS (ESI) m/e 391.9 [(M+H)+, calcd for C22H24F3NO2, 392.2]; LC/MS retention time (method E): tR=2.49 min.

후처리

  1. customThe reaction mixture was quenched by addition of saturated aqueous ammonium chloride at 0° C
  2. extractionThe reaction mixture was then extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f8f3d0f81c3147a8aff8148abf1347a2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703953B2

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