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

HRID 2182851
Notes
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Reaction equation

HRID 2182851 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e8afe313df00432f94bae2defb26bbb0
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06897227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes