Lithium hydroxide, monohydrate → HCID 11581125, compound

HRID 2247313Notes

Reaction equation

HRID 2247313 reaction equation
[CH:1]1([NH:7][C:8](=[O:26])[C:9]([S:12][C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=2)([CH3:11])[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].O>C1COCC1.CO>[CH:1]1([NH:7][C:8](=[O:26])[C:9]([S:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)([CH3:11])[CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11703599HCID 11703599, compound

Product 1

HCID 11581125HCID 11581125, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl (4-{[2-(cyclohexylamino)-1,1-dimethyl-2-oxoethyl]thio}phenoxy)acetate (prepared as example 72) was dissolved in THF/MeOH and treated with an aq. LiOH/H2O solution. The reaction mixture was stirred at rt for 16 h. The volatiles were removed in-vacuo and the residual aq. solution was acidified to pH=2 with a 1 N HCl solution. EtOAc was added and the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated to provide the desired carboxylic acid as a white solid. LCMS: (M+H)+=352.2.

Workup

  1. customThe volatiles were removed in-vacuo
  2. additionEtOAc was added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2acbae3c77ce4c8bb5ba72e822b826ee
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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