Water → 6-(2-Phenoxy-acetylamino)-n-hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

HRID 2182854Notes

Reaction equation

HRID 2182854 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:18]=[C:19](C)[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>C1C=CC=CC=1>[N+:22]([C:25]1[CH:26]=[C:27]([S:31]([CH2:34][CH2:35][O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:3]=[CH:2][CH:20]=[CH:19][CH:18]=2)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23]

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 695572526-(2-Phenoxy-acetylamino)-n-hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6-(2-phenoxyacetylamino)-n-hexanoic acid (made in analogy to Intermediate 15, 3.15 g, 11.9 mmol, 1.1 eq), 2-(m-nitrobenzenesulfonyl)ethanol (2.5 g, 10.8 mmol), and p-toluenesulfonic acid hydrate (0.5 g) in 100 mL of benzene was refluxed overnight with Dean-Stark trap. Thereafter water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure. The residual oil was purified by column chromatography (1% MeOH in CH2Cl2) to give 4.6 g (89%) of 6-(2-phenoxy-acetylamino)-n-hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester.

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
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residual oil was purified by column chromatography (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a230b368eb374b34b0afdd677a9857c8
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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