Water → HCID 19608701, compound

HRID 1781442Notes

Reaction equation

HRID 1781442 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13][O:14][C:15]=2[CH:16]([CH3:22])[C:17]([O:19]CC)=[O:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+].O.ClCCl>O1CCOCC1>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:13][O:14][C:15]=2[CH:16]([CH3:22])[C:17]([OH:19])=[O:18])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67596078HCID 67596078, compound

Product 1

HCID 19608701HCID 19608701, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]propanoate from Step 2 (198 mg, 0.495 mmol) and aqueous sodium hydroxide (10%, 0.30 mL) were dissolved in dioxane (15 mL). The solution was heated to reflux and held for 16 hours. Upon cooling to room temperature, water (20 mL) was added, and the solution was extracted with ether (2×30 mL). The combined ethereal solution was extracted with dilute sodium hydroxide (5%, 2×30 mL). All of the aqueous phases were combined and acidified with hydrochloric acid (conc.) to pH<2. The acidic aqueous phase was extracted with ether (2×30 mL). The final ether solution was dried over magnesium sulfate, filtered and evaporated under reduced pressure to yield a crude solid. Trituration with dichloromethane yielded crystals. The suspension was cooled to 0° C., filtered, washed with hexane and dried to yield [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]propanoic acid as a white crystalline solid (135 mg, 73%): mp 207° C. Mass spectrum: MH+=373. Anal. Calc'd. for C18H16N2O5S: C, 58.06; H, 4.33; N, 7.52; S, 8.61. Found: C, 57.87; H, 4.35; N, 7.49; S, 8.54.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. extractionthe solution was extracted with ether (2×30 mL)
  4. extractionThe combined ethereal solution was extracted with dilute sodium hydroxide (5%, 2×30 mL)
  5. extractionThe acidic aqueous phase was extracted with ether (2×30 mL)
  6. dry with materialThe final ether solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto yield a crude solid
  10. temperatureThe suspension was cooled to 0° C.
  11. filtrationfiltered
  12. washwashed with hexane
  13. customdried

Sources & evidence

ORD record
ord-e85dfcfdecae461d93dac45081928234
Source dataset
uspto-grants-1997_05
Patent number
US05633272

Reaction notes

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