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Triethylamine → N-[2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethyl]-2-pyridin-4-yl-acetamide

HRID 378979
ノート
印刷プレビュー

反応式

HRID 378979 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.[CH2:11](N(CC)CC)C.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=[N:24][C:22]=2[CH:23]=1.[CH2:28]1[CH2:33]CC(N=C=NC2CCCCC2)C[CH2:29]1.[O:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>O>[CH:45]1([O:46][C:47]2[C:48]([O:43][CH3:11])=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:22][NH:24][C:8](=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:44][CH2:33][CH2:28][CH2:29]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 312751,4-Dioxane2 回HCID 342284-Pyridineacetic acidHCID 757711-Hydroxybenzotriazole

生成物 1

HCID 21697280N-[2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethyl]-2-pyridin-4-yl-acetamide収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A suspension under nitrogen of 4-pyridin-acetic acid (0.43 g, 2.48 mmoles) hydrochloride in dioxane (20 ml) was added with triethylamine (0.34 ml, 0.25 g, 2.48 mmoles) and heated in water-bath to 40° C. for 10 minutes, then cooled and added with HOBT (0.33 g, 2.48 mmoles) and DCC (0.51 g, 2.48 mmoles). After 45 minutes a solution of 2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethylanine (0.53 g, 2.25 mmoles), obtained as described in example 3 then desalted, in dioxane (5 ml) was dropped therein. After 1 hour the formed solid was filtered and washed with dioxane, then dried, taken up in ethyl acetate, filtered and washed with aqueous NaHCO3, then with water. The mother liquor was anhydrified and dried to give an oil which was purified by flash chromatography (eluent: methylene chloride/methanol 99:1 to 93:7) to give 0.57 g of the title product (yield: 71%).

後処理

  1. temperaturecooled
  2. customobtained
  3. additionwas dropped
  4. filtrationAfter 1 hour the formed solid was filtered
  5. washwashed with dioxane
  6. customdried
  7. filtrationfiltered
  8. washwashed with aqueous NaHCO3
  9. customdried
  10. customto give an oil which
  11. customwas purified by flash chromatography (eluent: methylene chloride/methanol 99:1 to 93:7)

出典と根拠

ORDレコード
ord-858604581c2645ffafcb50cbc00df785
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06297257B1

反応ノート

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