Sodium Hydroxide → HCID 22261619, compound

HRID 1610730Notes

Reaction equation

HRID 1610730 reaction equation
[OH:1][CH:2]([C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:26][CH:27]=1)[CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])[CH:11]=1)[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>O1CCCC1CCO>[OH:1][CH:2]([C:23]1[N:24]=[C:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[S:26][CH:27]=1)[CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:21])([F:22])[CH:18]([F:19])[F:20])[CH:11]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261585HCID 22261585, compound

Product 1

HCID 22261619HCID 22261619, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of ethyl 3-hydroxy-3-(2-phenyl-1,3-thiazol-4-yl)-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionate (6.28 g, 13.0 mmol) in tetrahydrofuran-ethanol (20 ml—20 ml) was added 2N sodium hydroxide (17 ml, 34 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure and diluted with water. The aqueous layer was washed with ether and acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-hydroxy-3-(2-phenyl-1,3-thiazol-4-yl)-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionic acid (5.51 g, 93%) as a pale-yellow oil.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. additiondiluted with water
  4. washThe aqueous layer was washed with ether
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42f6d8525a3d44cd849582bede98ef89
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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