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

HRID 2182851
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HRID 2182851 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-HCID 521998p-Toluenesulfonic acid monohydrateHCID 224793366-[2-(3,5-Dimethylphenoxy)acetamido]hexanoic acid2회

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e8afe313df00432f94bae2defb26bbb0
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06897227B2

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