Lithium hydroxide, monohydrate → HCID 68328073, compound

HRID 2281238Notes

Reaction equation

HRID 2281238 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])[N:12]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68327815HCID 68327815, compound

Product 1

HCID 68328073HCID 68328073, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of ethyl 2-(2-(4-fluorophenyl)thiazol-4-yl)-2-methylpropanoate (4.56 g, 15.5 mmol) in 1:1:1 THF/ethanol/water (45 mL) was added lithium hydroxide monohydrate (2.93 g, 69.8 mmol). The reaction was stirred overnight, concentrated and redissolved in water (175 mL). The solution was washed with ether (1×100 mL), acidified by the addition of 1.0 N HCl (80 mL) and extracted with ethyl acetate (2×70 mL). The combined extracts were dried (Na2SO4) and concentrated to afford 2-(2-(4-fluorophenyl)thiazol-4-yl)-2-methylpropanoic acid as a white solid (4.04 g, 98%). This material was used in the next step without purification.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in water (175 mL)
  3. washThe solution was washed with ether (1×100 mL)
  4. additionacidified by the addition of 1.0 N HCl (80 mL)
  5. extractionextracted with ethyl acetate (2×70 mL)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-608a545379a342b7837ad2a6a041886c
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

Loading…