Methanesulfonic Acid → HCID 53826538, compound

HRID 1604702Notes

Reaction equation

HRID 1604702 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:35]=[C:34]([O:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:32][C:22]=4[O:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CS(O)(=O)=O>C(#N)C.CC(C)=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:35]=[C:34]([O:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:32][C:22]=4[O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 17822415HCID 17822415, compound

Product 1

HCID 53826538HCID 53826538, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-4-[3-(ethoxycarbonyl)propoxy]phenoxyacetate (200 mg) was dissolved in a mixed solvent of acetnitrile (10 ml) and acetone (1 ml) and methanesulfonic acid (62 mg) was added. The resulting solution was stirred at 80° C. for two hours. The reaction mixture was concentrated and diluted with water and neutralized with sodium hydrogen carbonate solution. The mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and was dried over magnesium sulfate. After concentration, the product was crystallized with a mixed solvent of diisopropyl ether and n-hexane (1:2), filtered and dried to give 2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-4-[3-(ethoxycarbonyl)propoxy]-phenoxyacetic acid (117 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water and neutralized with sodium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationAfter concentration
  8. customthe product was crystallized with a mixed solvent of diisopropyl ether and n-hexane (1:2)
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-eab1eec02d134845ab509b02701da19d
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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