Triethylamine → HCID 178521402, 화합물

HRID 37309노트

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HRID 37309 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([O:27][CH2:28][C:29](O)=[O:30])[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)CCOCC1.[K+].[Br-]>ClCCl.CN(C)C1C=CN=CC=1>[CH:15]1([O:27][CH2:28][C:29]([C:1]2[C:6](=[O:7])[S:5][CH2:4][C:2]=2[OH:3])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 253877Potassium BromideHCID 10214383Thiotetronic acidHCID 193718122-(Cyclododecyloxy)acetic acid

생성물 1

HCID 178521402HCID 178521402, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 0.37 g (3.2 mmol) of thiotetronic acid in 20 mL of dry dichloromethane at 0° C. is added 0.4 mL (2.9 mmol) of triethylamine followed by 0.11 g (0.9 mmol) of 4-dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 0.7 g (2.9 mmol) of cyclododecyloxyacetic acid is added, followed by 1.35 g (3.2 mmol) of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate. 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. The layers are separated and the organic layer is washed twice with aqueous sodium bicarbonate and then twice with 2N HCl. The organic phase is then dried over MgSO4 and the dichloromethane evaporated. The residue is flash chromatographed on acidic silica gel using 50% ether/hexanes and then recrystallized from hexanes to give a yellow solid: m.p. 93°-95° C.; IR (KBr) 2920, 2840, 1690, 1660, 1580 cm-1 ; NMR (DMSO-d6) δ 1.2-1.6 (m, 10H), 3.4 (m, 1H), 3.95 and 4.4 (s, 2H), 4.6 (bs, 2H); MS (EI) M+340.

후처리

  1. customAfter 10 minutes the ice bath is removed
  2. stirringto stir overnight
  3. customThe reaction mixture is quenched with 1N HCl
  4. customThe layers are separated
  5. washthe organic layer is washed twice with aqueous sodium bicarbonate
  6. dry with materialThe organic phase is then dried over MgSO4
  7. customthe dichloromethane evaporated
  8. customchromatographed on acidic silica gel using 50% ether/hexanes
  9. customrecrystallized from hexanes
  10. customto give a yellow solid

출처 및 근거

ORD 기록
ord-0efddcf39af742ba8904a02de25d26d3
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420153

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