Lithium Hydroxide → HCID 57652730, compound

HRID 424831Notes

Reaction equation

HRID 424831 reaction equation
COC(=O)C1C=CC=C([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]=[N:25][C:26]=3[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=2[CH3:38])([CH3:13])[CH3:12])C=1.[OH-:40].[Li+].[O:42]1[CH2:47][CH2:46]OCC1>>[Cl:37][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([Cl:36])[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:14]3[CH:15]=[CH:16][C:46]([C:47]([OH:42])=[O:40])=[CH:12][CH:11]=3)([CH3:13])[CH3:12])=[C:15]([CH3:38])[CH:16]=2)=[C:26]([CH:27]([CH3:28])[CH3:29])[N:25]=[N:24]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 66704205HCID 66704205, compound

Product 1

HCID 57652730HCID 57652730, compoundYield 99%

Conditions

Temperature
50 °C

Procedure

To an ambient temperature solution of 3-(1-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-1-methyl-ethylsulfanyl)-benzoic acid methyl ester (110 mg, 0.188 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (282 μL, 0.564 mmol, 2.0N in water). The reaction is heated to 50° C. for 2 h. The reaction is concentrated and the residue is diluted with Et2O and water. The aqueous layer is adjusted to pH ˜4 and 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 (106 mg, 99%). LC/MS (ES+): 570.0, 100.0%.

Workup

  1. concentrationThe reaction is concentrated
  2. additionthe residue is diluted with Et2O and water
  3. extractionextracted 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-66d28e1fb2f44229b3acd32f4d65760c
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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