Lithium Hydroxide → HCID 67528716, compound

HRID 2261858Notes

Reaction equation

HRID 2261858 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]([C:29]4[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:36])[N:23]=[CH:24][C:25]=3[CH:26]([CH3:28])[CH3:27])=[CH:15][C:14]=2[CH3:37])[CH3:12])[CH:5]=1.[OH-:39].[Li+].[O:41]1[CH2:46]COCC1>>[Cl:35][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:36])[C:29]=1[N:22]1[C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH:11]([S:10][C:6]3[CH:5]=[CH:4][C:9]([C:46]([OH:41])=[O:39])=[CH:8][CH:7]=3)[CH3:12])=[C:14]([CH3:37])[CH:15]=2)=[C:25]([CH:26]([CH3:28])[CH3:27])[CH:24]=[N:23]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67528557HCID 67528557, compound

Product 1

HCID 67528716HCID 67528716, compound

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}-ethylsulfanyl)-benzoic acid methyl ester (10 mg, 0.0176 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (26 μL, 0.052 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 (10 mg, quant). ES/MS m/e (35Cl) 556.3 (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-217061455e3947ebb58aa32592284447
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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