Hydrochloric Acid → HCID 58088347, compound

HRID 250287Notes

Reaction equation

HRID 250287 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[C:19]([C:26]4[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][C:27]=4[F:36])=[N:20][O:21][C:22]=3[CH:23]3[CH2:25][CH2:24]3)=[CH:12][C:11]=2[CH3:37])=[N:7][C:6]=1[CH3:38])=[O:4].[Li+].[OH-].Cl>CO.C1COCC1.O>[CH:23]1([C:22]2[O:21][N:20]=[C:19]([C:26]3[C:31]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:29]=[CH:28][C:27]=3[F:36])[C:18]=2[CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]([C:8]3[S:9][C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:38])[N:7]=3)=[C:11]([CH3:37])[CH:12]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58088345HCID 58088345, compound

Product 1

HCID 58088347HCID 58088347, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-(4-(5-Cyclopropyl-3-(2-fluoro-6-trifluoromethyl-phenyl)-isoxazol-4-ylmethoxy)-2-methyl-phenyl)-4-methyl-thiazole-5-carboxylic acid methyl ester (0.025 g, 0.046 mmol) in 1 mL of methanol and 1 mL of THF is added a solution of LiOH (0.011 g, 0.46 mmol) in water (11 mL). The reaction is heated to 55° C. for 30 minutes. The reaction is cooled, acidified with aqueous 1M HCl, and extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered, and evaporated to yield the title compound (24 mg, 99%). ES/MS m/e 533.0 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-85fc4d16cafc41a683fe1b4405eba605
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

Loading…