Methanol → HCID 58088353, compound

HRID 250291Notes

Reaction equation

HRID 250291 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[C:23]([C:30]5[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=5[Cl:37])=[N:24][O:25][C:26]=4[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=3[CH3:38])=[CH:11][CH:12]=2)[N:7]([CH2:39][CH2:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:6]=1)=[O:4].CO.[OH-].[Na+]>C1COCC1>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[C:23]1[C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([C:10]3[CH:9]=[C:8]4[C:13]([C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]4[CH2:39][CH2:40][S:41]([CH3:44])(=[O:42])=[O:43])=[CH:12][CH:11]=3)=[C:15]([CH3:38])[CH:16]=2)=[C:26]([CH:27]([CH3:29])[CH3:28])[O:25][N:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58088359HCID 58088359, compound

Product 1

HCID 58088353HCID 58088353, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1-(2-methanesulfonyl-ethyl)-1H-indole-3-carboxylic acid methyl ester (235 mg, 0.358 mmol), methanol (17 mL), THF (8 mL), and 5 N sodium hydroxide (1.29 mL) is heated at reflux for two days. The mixture is allowed to cool and is concentrated under reduced pressure to near dryness. Approximately 10 mL of water is added and the mixture is stirred for two hours. The mixture is filtered and the solid is washed with water and dried to provide the title compound (187 mg, 81%). LCMS (ES+): (641.0).

Workup

  1. temperatureis heated
  2. temperatureat reflux for two days
  3. temperatureto cool
  4. concentrationis concentrated under reduced pressure
  5. additionApproximately 10 mL of water is added
  6. filtrationThe mixture is filtered
  7. washthe solid is washed with water
  8. customdried

Sources & evidence

ORD record
ord-f0d621cd76e040818eea7cefb58da078
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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