Water → HCID 69241992, 화합물

HRID 1394131노트

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HRID 1394131 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:26][N:27](C=O)C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:26]#[N:27])[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 6228DimethylformamideHCID 87425656HCID 87425656, 화합물

생성물 1

HCID 69241992HCID 69241992, 화합물

시약·촉매·용매 1

HCID 165872Tetrabutylammonium Cyanide촉매

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온도
50 °C

실험 절차

To a solution of Example 17B (16.55 g, 44 mmol) in dry DMF (100 mL) under nitrogen was added tetrabutylammonium cyanide (50 g, 200 mmol). The mixture was heated to 50° C. for 60 hours and then poured into cold water and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane to provide the titled compound (12 g). MS (ESI) m/e 312 (M+H)+, 310 (M−H)−; 1H NMR (400 MHz, CD3OD) δ ppm 1.44 (m, 9H) 2.10 (m, 1H) 2.79 (m, 1H) 3.05 (m, 1H) 3.17 (m, 1H) 3.33 (m, 1H) 3.57 (dd, 1H) 3.83 (m, 2H) 3.96 (m, 1H) 4.48 (m, 1H) 4.65 (m, 2H).

후처리

  1. extractionextracted with ethyl acetate (3×250 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane

출처 및 근거

ORD 기록
ord-d386c51c6fa74d5ba0d4b64ee60d39e1
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348346B2

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