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

HRID 11479
ノート
印刷プレビュー

反応式

HRID 11479 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-15 °C

実験手順

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, a saturated aqueous sodium hydrogencarbonate solution (70 ml) and ethyl acetate (70 ml) were added to the reaction mixture, and the reaction mixture was distributed. The ethyl acetate layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure to give 1.3 g (quantitatively) of 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as a oily matter.

後処理

  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 and dried over anhydrous magnesium sulfate
  4. concentrationThe ethyl acetate layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-7be440cf55a742dbbf2f5f861b28233a
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07098226B2

反応ノート

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