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Bromoacetic Acid → 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 18409
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HRID 18409 반응식
[Br:1][CH2:2][C:3]([OH:5])=O.CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[C:22]12([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[C:22]12([CH2:32][CH2:33][N:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:3](=[O:5])[CH2:2][Br:1])[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2
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참가 물질

8

반응물 5

HCID 6227Bromoacetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

생성물 1

HCID 574798992-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
-15 °C

실험 절차

Bromoacetic acid (0.50 g, 3.6 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml), and the solution was stirred at −15° C. under a nitrogen atmosphere. N-Methylmorpholine (0.40 ml, 3.6 mmol) and isobutyl chlorocarbonate (0.45 ml, 3.5 mmol) were added to the solution. Then a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 1.0 g, 3.5 mmol) in anhydrous tetrahydrofuran (20 ml) was added dropwise to the mixture. The whole was stirred at 0° C. for 1.5 hours, then a saturated aqueous sodium hydrogencarbonate solution (70 ml) and ethyl acetate (70 ml) were added to the reaction mixture to distribute it. The ethyl acetate layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, quantitatively) as an oily matter.

후처리

  1. stirringThe whole was stirred at 0° C. for 1.5 hours
  2. washThe ethyl acetate layer was washed with water (70 ml)
  3. dry with materiala saturated aqueous sodium chloride solution (70 ml) successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e19bd88eb6a84b79b364774825249667
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741346B2

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