Lithium Hydroxide → HCID 69689647, compound

HRID 343080Notes

Reaction equation

HRID 343080 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:13][O:14][C:15]=2[CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Li+]>O1CCCC1.CO.O>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:13][O:14][C:15]=2[CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54498440HCID 54498440, compound

Product 1

HCID 69689647HCID 69689647, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 4-[[4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]methoxy]benzoate (Example 50) (65.0 mg, 0.14 mmol) was dissolved in tetrahydrofuran/methanol/water (5.0 mL 7:2:1) and lithium hydroxide (10 mg, 0.250 mmol) was added. The solution was heated to reflux for 4 hours and cooled to room temperature. The solvent was removed in vacuo and the crude product was purified by preparative high pressure liquid chromatography using a C18 reverse phase column. The appropriate factions were combined and concentrated to afford pure 4-[[4-[4(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]methoxy]benozoic acid as a white crystalline material (38 mg, 60%): mp 206.4°-207.9° C. 1H NMR CD3OD 5.29 (S, 2H), 7.01 (d, 2H, 8.4 Hz), 7.25-7.45 (m, 7H), 7.84-7.97 (m, 4H). Mass spectrum calc'd. for C23H18N2O6S: 450. Found: 451 (m+H+).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 4 hours
  3. customThe solvent was removed in vacuo
  4. customthe crude product was purified by preparative high pressure liquid chromatography
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0867069ddc24f39ab18a5a1c7699417
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

Loading…