Sodium ethoxide → HCID 69313539, compound

HRID 898479Notes

Reaction equation

HRID 898479 reaction equation
CC[O-].[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][CH:35]=[CH:34][CH:33]=2)=[N:29][C:28]=1[CH2:38]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][CH2:38][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 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonateHCID 86587408HCID 86587408, compound

Product 1

HCID 69313539HCID 69313539, compoundYield 17.1%

Procedure

Freshly prepared NaOEt (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-phenyloxazol-4-yl)-ethyl ester (572 mg, 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 EtOAc/water. After a second water wash, the organic layer was dried (MgSO4) and concentrated to give 500 mg crude product. Purification by flash chromatography (15% EtOAc/hexane) provided the product (98 mg, 17%): Rf=0.32 in 15% EtOAc/hexane; MS m/e 426 (MH+).

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
  8. customto give 500 mg crude product
  9. customPurification by flash chromatography (15% EtOAc/hexane)

Sources & evidence

ORD record
ord-12a7ee3d4c0e4dcfa2d9e5ac47aeb6ef
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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