Lithium Hydroxide → 5-(4-(5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid

HRID 250285Notes

Reaction equation

HRID 250285 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[C:19]([C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:33])=[N:20][O:21][C:22]=3[CH:23]3[CH2:25][CH2:24]3)=[CH:12][C:11]=2[CH3:34])=[CH:8][CH:9]=1)=[O:4].[OH-].[Li+]>CO.C1COCC1.O.Cl>[CH:23]1([C:22]2[O:21][N:20]=[C:19]([C:26]3[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=3[Cl:32])[C:18]=2[CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]([C:7]3[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)=[C:11]([CH3:34])[CH:12]=2)[CH2:24][CH2:25]1

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 580883565-(4-(5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 580883515-(4-(5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 5-(4-(5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-thiophene-2-carboxylic acid methyl ester (0.138 g, 0.27 mmol) in 3 mL of methanol and 3 mL of THF is added a solution of lithium hydroxide (0.06 g, 2.7 mmol) in 3 mL of water. The reaction is heated to 55° C. for 1 hour. The solvent is evaporated to give a white solid. The solid is dissolved in aqueous 1M HCl and is extracted with ethyl acetate. The organic layer is washed with brine and dried over sodium sulfate. The reaction is filtered and concentrated under reduced pressure to yield the title compound. ES/MS m/e 500.0; 498.1 (M+1).

Workup

  1. customThe solvent is evaporated
  2. customto give a white solid
  3. extractionis extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe reaction is filtered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-074306db69a94157992310900dfa5a0f
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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