Triethylamine → HCID 178520549、化合物

HRID 2380366ノート

反応式

HRID 2380366 の反応式
[CH2:1]1[C:6](=[O:7])[S:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[CH:15]1([CH:27]([CH2:31][CH3:32])C(O)=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CC[O:48][CH2:47]C1>ClCCl.CN(C)C1C=CN=CC=1>[CH:15]1([CH2:27][CH2:31][CH2:32][C:47]([C:1]2[C:6](=[O:7])[S:5][CH2:4][C:2]=2[OH:3])=[O:48])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 10214383Thiotetronic acidHCID 19371806Cyclododecylbutanoic acid

生成物 1

HCID 178520549HCID 178520549、化合物収率 33.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a dry flask under N2 atmosphere at 0° C. is added 1.31 g (11.3 mmol) of thiotetronic acid in 40 mL of dry dichloromethane followed by 1.42 mL (10.2 mmol) of triethylamine and 0.38 g (3.1 mmol) of 4-dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 2.6 g (10.2 mmol) of cyclododecylbutanoic acid is added followed by 4.8 g (11.3 mmol) of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho p-toluenesulfonate. After stirring for 10 minutes, the reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is quenched with 1N HCl. The layers are separated and the aqueous phase is washed once with dichloromethane. The combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl. The organic phase is then dried over MgSO4 and the dichloromethane evaporated. The residue is flash chromatographed on acidic silica gel using 8% ether/hexanes, dissolved in ether, washed with 1N HCl, dried and evaporated to give 1.2 g of a white solid: m.p. 62°-69° C.; IR; NMR (CDCl3) δ1.2-1.4 (m, 10H), 1.5 (s, 4H), 1.65 (m, 2H), 2.9 (t, 2H, J=7 Hz), 3.9 (s, 2H); MS Anal. Calc'd. for C20H32O3S: C, 68.53; H, 8.63 Found: C, 67.72; H, 8.84

後処理

  1. stirringAfter stirring for 10 minutes
  2. temperatureto warm to room temperature
  3. stirringis stirred overnight
  4. customThe reaction mixture is quenched with 1N HCl
  5. customThe layers are separated
  6. washthe aqueous phase is washed once with dichloromethane
  7. washThe combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl
  8. dry with materialThe organic phase is then dried over MgSO4
  9. customthe dichloromethane evaporated
  10. customchromatographed on acidic silica gel using 8% ether/hexanes
  11. dissolutiondissolved in ether
  12. washwashed with 1N HCl
  13. customdried
  14. customevaporated

出典と根拠

ORDレコード
ord-2aa7c60317e34fe2bd19775ebc4feaa2
出典データセット
uspto-grants-1994_11
特許番号
US05366993

反応ノート

読み込み中…