Sodium ethoxide → HCID 69313539, compound

HRID 398193Notes

Reaction equation

HRID 398193 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][C:8](=[O:25])[C:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20](=O)N(C)C)=[CH:15][CH:14]=1)([CH3:11])[CH3:10])[CH3:6].[CH3:26][C:27]1[O:31][C:30]([C:32]2[CH:37]=[CH:36][C:35](C3C=CC=CC=3)=[CH:34][CH:33]=2)=[N:29][C:28]=1[CH2:44]COS(C1C=CC(C)=CC=1)(=O)=O>>[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH3:10])([O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19][CH2:20][CH2:44][C:28]2[N:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:31][C:27]=2[CH3:26])=[CH:17][CH:18]=1)[CH3:11])[CH3:6]

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 12966835Toluene-4-sulfonic acid 2-(2-biphenyl-4-yl-methyl-oxazol-4-yl)ethyl esterHCID 86587408HCID 86587408, compound

Product 1

HCID 69313539HCID 69313539, compoundYield 87%

Procedure

Freshly prepared sodium ethoxide (from 50 mg (2.2 mmol) Na) was charged with 2-(4-dimethylcarbamoylsulfanyl-phenoxy)-2-methyl-propionic acid ethyl ester (420 mg, 1.35 mmol) and refluxed for 3 h. Toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-yl)-ethyl ester (2.2 mmol) was added and the mixture was refluxed for another 3 h. The reaction was cooled and concentrated. The residue was shaken with ethyl acetate/water. After a second water wash, the organic layer was dried (MgSO4) and concentrated to give 500 mg crude product.

Workup

  1. temperaturerefluxed for 3 h
  2. temperaturethe mixture was refluxed for another 3 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. washAfter a second water wash
  6. dry with materialthe organic layer was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f23698b508d44df9e103a6833227ab9
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

Loading…