Triethylamine → HCID 178472454, 화합물

HRID 470699노트

반응식

HRID 470699 반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:20][Si:21]([CH3:36])([CH3:35])[CH2:22][CH2:23][O:24][C:25](ON1C(=O)CCC1=O)=[O:26]>O1CCOCC1.O>[CH3:20][Si:21]([CH3:36])([CH3:35])[CH2:22][CH2:23][O:24][C:25]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:26]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 178472434HCID 178472434, 화합물

생성물 1

HCID 178472454HCID 178472454, 화합물수율 98.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Ethyl trans-4-aminocyclohexanecarboxylate (J. Med. Chem., 1971, 14, 600-614) (29.5 g, 143 mmol) was dissolved in 1,4-dioxane (290 ml) and water (290 ml), triethylamine (30.0 ml, 215 mmol) and 1-[2-(trimethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (40.8 g, 157 mmol) were added under ice cooling and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated and then the residue was diluted with ethyl acetate and washed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give 44.3 g (98%) of the title compound as colorless needle-like crystals.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6aa9c9252ff14453a70ea5920a304210
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629133B2

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