Methanol → HCID 58088341, compound

HRID 250283Notes

Reaction equation

HRID 250283 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)[NH:7][CH:6]=1)=[O:4].[OH-].[Na+].CO.C1COCC1>O>[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][NH:7]4)=[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

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58088350HCID 58088350, compound

Product 1

HCID 58088341HCID 58088341, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl ester (80 mg, 0.15 mmol), 5 N sodium hydroxide (150 μL, 0.750 mmol), methanol (2 mL) and THF (1 mL) is heated at 85° C. for five hours. The mixture is cooled and 5 mL of water is added and the volatile solvents are evaporated under reduced pressure. The basic layer is washed with ether and then acidified with 1 N HCl and extracted with ether. The second ether layers are dried over anhydrous magnesium sulfate, are concentrated, and are crystallized from ether-hexane to provide 42 mg (54%) of the title compound. LC-ES/MS m/e 535.0 (M+1), 93.2% purity.

Workup

  1. temperatureThe mixture is cooled
  2. customthe volatile solvents are evaporated under reduced pressure
  3. washThe basic layer is washed with ether
  4. extractionextracted with ether
  5. dry with materialThe second ether layers are dried over anhydrous magnesium sulfate
  6. concentrationare concentrated
  7. customare crystallized from ether-hexane

Sources & evidence

ORD record
ord-20df775f2d614614ae3ddaaae5c12133
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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