Triethylamine → HCID 178520537、化合物

HRID 129537

反応式

HRID 129537 の反応式
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:24]1([CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN(C)CCCN=C=NCC>CN(C)C=O>[CH:24]1([CH2:30][CH2:31][CH2:32][C:33]([C:1]2[C:6](=[O:7])[O:5][CH2:4][C:2]=2[OH:3])=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 75200Cyclohexanebutanoic acidHCID 521261Tetronic acid

生成物 1

HCID 178520537HCID 178520537、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1.0 g (10.0 mmol) of tetronic acid in 30 mL of dry N,N-dimethylformamide at 0° C. is added 1.5 mL (11 mmol) of triethylamine followed by 0.37 g (30 mmol) of 4 dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 2.0 g (11.7 mmol) of 4-cyclohexyl butyric acid is added, followed by 2.25 g (11.7 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide. After 10 minutes, the ice bath is removed and the reaction mixture is allowed to stir overnight. The reaction mixture is quenched with 1N HCl and the solution is washed three times with hexanes. The combined organic layers are washed with water, dried over magnesium sulfate and evaporated. The residue is flash chromatographed on silica gel using 5% methanol/ethyl acetate with 2 mL of acetic acid/liter to give an orange solid: m.p. 38-42° C.; IR (film) 2920, 2840, 1770, 1690, 1660, 1600 cm-1 ; NMR (CDCl3) δ 0.9 (m, 2H), 1.2 (m, 6H), 1.7 (m, 6H), 2.9 (q, J=7 Hz, 2H), 4.6 and 4.7 (s, 2H), 12.1 (bs, 1H); MS (EI): M+ 252.

後処理

  1. waitAfter 10 minutes
  2. customthe ice bath is removed
  3. stirringto stir overnight
  4. customThe reaction mixture is quenched with 1N HCl
  5. washthe solution is washed three times with hexanes
  6. washThe combined organic layers are washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customchromatographed on silica gel using 5% methanol/ethyl acetate with 2 mL of acetic acid/liter
  10. customto give an orange solid

出典と根拠

ORDレコード
ord-8fbe33a69b7f439888f617d849ad99cf
出典データセット
uspto-grants-1995_11
特許番号
US05468774

関連ノート

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