Ethanol, 2-[(3-nitrophenyl)sulfonyl]- → HCID 131724894, compound

HRID 2182859Notes

Reaction equation

HRID 2182859 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:10])([CH3:3])[CH3:2].[N+:21]([C:24]1[CH:25]=[C:26]([S:30]([CH2:33][CH2:34]O)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[N+:21]([C:24]1[CH:25]=[C:26]([S:30]([CH2:33][CH2:34][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[CH2:8][O:7][C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-HCID 521998p-Toluenesulfonic acid monohydrateHCID 433550084-{2-[3-(Propan-2-yl)phenoxy]acetamido}butanoic acid2×

Product 1

HCID 131724894HCID 131724894, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-(3-isopropylphenoxyactamido)butyric acid (Intermediate 24, 3.1 g, 11.1 mmol, 1.1 eq), 2-(3-nitrobenzenesulfonyl)ethanol (2.3 g, 10.0 mmol), and TsOH.H2O (0.5 g) in 100 mL of benzene was heated overnight to reflux temperature with a Dean-Stark trap. Thereafter the mixture was concentrated by evaporation and the resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to give Intermediate 25 (4.8 g, 97%) as a light yellow oil which solidified on standing.

Workup

  1. temperaturewas heated overnight
  2. temperatureto reflux temperature with a Dean-Stark trap
  3. concentrationThereafter the mixture was concentrated by evaporation
  4. customthe resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a8188dd6656845348b22173d5e7a57bd
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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