Sulfuric Acid → Tesaglitazar

HRID 1384419Notes

Reaction equation

HRID 1384419 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][S:34]([CH3:37])(=[O:36])=[O:35])=[CH:29][CH:28]=2)=[CH:20][CH:19]=1)[C:5](N[C@H](C1C=CC=CC=1)CO)=[O:6])[CH3:2].S(=O)(=O)(O)[OH:39].O1CCOCC1>O>[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][S:34]([CH3:37])(=[O:35])=[O:36])=[CH:31][CH:32]=2)=[CH:22][CH:23]=1)[C:5]([OH:6])=[O:39])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 20670106HCID 20670106, compound

Product 1

HCID 208901TesaglitazarYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(S)-2-Ethoxy-N-(2-hydroxy(R)-1-phenylethyl)-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic amide (4.49 g; 8.59 mmole), concentrated sulfuric acid (12.5 Ml), dioxan (50 ml) and water (50 ml) were stirred at 80° C. for 6 hours. After cooling, water (100 ml) was added and the product was extracted with dichloromethane (2×100 ml). The organic phases were combined and washed with brine (60 ml), dried (sodium sulfate), filtered and evaporated in vacuo. Purification by chromatography on silica gel using heptan:ethyl acetate:acetic acid (10:10:1) as gradient and azeotropic destillation with toluen gave 2.78 g (yield 79%) of (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with dichloromethane (2×100 ml)
  3. washwashed with brine (60 ml)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-2a137a69a1fa4a00a41be2e3f8bda3b9
Source dataset
uspto-grants-2001_07
Patent number
US06258850B1

Reaction notes

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