Water → HCID 69241992、化合物

HRID 1394131ノート

反応式

HRID 1394131 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 87425656HCID 87425656、化合物

生成物 1

HCID 69241992HCID 69241992、化合物

試薬・触媒・溶媒 1

HCID 165872Tetrabutylammonium Cyanide触媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d386c51c6fa74d5ba0d4b64ee60d39e1
出典データセット
uspto-grants-2008_03
特許番号
US07348346B2

反応ノート

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