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Water → 6-[2-(3,5-Dimethyl-phenoxy)acetylamino]hexanoic Acid 2-(3-nitrobenzenesulfonyl)ethyl Ester

HRID 2182851
ノート
印刷プレビュー

反応式

HRID 2182851 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[O:5][CH2:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:8].[N+:22]([C:25]1[CH:26]=[C:27]([S:31]([CH2:34][CH2:35]O)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N+:22]([C:25]1[CH:26]=[C:27]([S:31]([CH2:34][CH2:35][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:18]=[C:19]([CH3:21])[CH:20]=[C:2]([CH3:1])[CH:3]=2)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-HCID 521998p-Toluenesulfonic acid monohydrateHCID 224793366-[2-(3,5-Dimethylphenoxy)acetamido]hexanoic acid2 回

生成物 1

HCID 695572376-[2-(3,5-Dimethyl-phenoxy)acetylamino]hexanoic Acid 2-(3-nitrobenzenesulfonyl)ethyl Ester収率 94.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 6-[2-(3,5-dimethyl-phenoxy)acetylamino]hexanoic acid (Intermediate 15, 3.0 g, 10.2 mmol), 2-(m-nitrobenzenesulfonyl)ethanol (available from Aldrich 2.3 g, 10.0 mmol), and p-toluenesulfonic acid hydrate (0.5 g) in 100 mL of toluene was refluxed overnight with Dean-Stark trap. Then water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 solution two times, dried over anhydrous MgSO4, and concentrated under reduced pressure. The resulting residual oil was purified by column chromatography (1% MeOH in CH2Cl2) to give Intermediate 16 (4.8 g, 89%) as a yellowish thick oil.

後処理

  1. temperaturewas refluxed overnight with Dean-Stark trap
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe combined organic layers were washed with saturated NaHCO3 solution two times
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residual oil was purified by column chromatography (1% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-e8afe313df00432f94bae2defb26bbb0
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06897227B2

反応ノート

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