Triethylamine → HCID 178520549, 화합물

HRID 129535노트

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HRID 129535 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 178520549HCID 178520549, 화합물수율 33.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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) δ 1.2-1.4 (m, 10H), 1.5 (s, 4H), 1.65 (m, 2H), 2.9 (t, 2H, J=7 Hz), 3.96 (s, 2H); MS.

후처리

  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

출처 및 근거

ORD 기록
ord-c9697368bb1d44f0b218071009af0f88
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468774

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