Lithium hydroxide, monohydrate → HCID 86660070, compound

HRID 2408259Notes

Reaction equation

HRID 2408259 reaction equation
[F:1][CH:2]([F:31])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][C:17]([C:21]3[S:22][CH:23]=[C:24]([C:26]([O:28]CC)=[O:27])[N:25]=3)([F:20])[CH2:16][CH2:15]2)=[O:13])[N:4]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:31][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:15][CH2:16][C:17]([C:21]3[S:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=3)([F:20])[CH2:18][CH2:19]2)=[O:13])[N:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67470620HCID 67470620, compound

Product 1

HCID 86660070HCID 86660070, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}-4-fluoropiperidin-4-yl)-1,3-thiazole-4-carboxylate (300 mg) in tetrahydrofuran (3 ml) and water (1 ml) was added, at room temperature, lithium hydroxide monohydrate (40 mg). The mixture was stirred at room temperature for 3 hours, and then ice-cold 1N HCl solution was added. The aqueous phase was extracted with ethyl acetate and then the combined organic phases were dried over sodium sulphate. The solids were filtered off and the solvent was distilled off. This gave 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}-4-fluoropiperidin-4-yl)-1,3-thiazole-4-carboxylic acid (230 mg).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. filtrationThe solids were filtered off
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d20af4264fff4adfaa0cb39842f126ec
Source dataset
uspto-grants-2014_08
Patent number
US08815775B2

Reaction notes

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