Lithium Hydroxide → HCID 57473614, compound

HRID 2261861Notes

Reaction equation

HRID 2261861 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])[N:24]=[CH:25][C:26]=3[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=2[CH3:38])([CH3:13])[CH3:12])[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[N:23]1[C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([C:11]([S:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:39])=[O:2])([CH3:13])[CH3:12])=[C:15]([CH3:38])[CH:16]=2)=[C:26]([CH:27]([CH3:29])[CH3:28])[CH:25]=[N:24]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57473613HCID 57473613, compound

Product 1

HCID 57473614HCID 57473614, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To an ambient temperature solution of 3-(1-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-1-methyl-ethylsulfanyl)-benzoic acid methyl ester (91 mg, 0.156 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (234 μL, 0.468 mmol, 2.0N in water). The reaction mixture is heated to 50° C. The reaction mixture is concentrated and the residue is partitioned between Et2O and water. The aqueous layer pH is adjusted to approximately 4 and is extracted with a second portion of Et2O. The combined organic layers are washed with water, dried (MgSO4), filtered, and concentrated to yield the title compound (84 mg, 95%). ES/MS m/e (35Cl) 569.0 (M+1)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionis extracted with a second portion of Et2O
  4. washThe combined organic layers are washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88d3136b8bcf40bc883f406f72e57b4f
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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