Sodium Hydroxide → (2'-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-2,5'-bi-1,3-thiazol-4-yl)acetic acid

HRID 561204Notes

Reaction equation

HRID 561204 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]3[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25]C)=[O:24])[N:21]=3)=[CH:15][N:16]=2)[CH2:8][CH2:7]1.[OH-].[Na+]>C1COCC1.CO>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]3[S:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=3)=[CH:15][N:16]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86620458Methyl (2'-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-2,5'-bi-1,3-thiazol-4-yl)acetate

Product 1

HCID 24988883(2'-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-2,5'-bi-1,3-thiazol-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl (2′-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-2,5′-bi-1,3-thiazol-4-yl)acetate (220 mg, 0.44 mmol) in THF/MeOH (4:1) (v/v) (5 mL) was treated with 1 N NaOH (1 mL, 1 mmol) and heated at reflux temperature for 2 h. Volatile materials were removed in vacuo. The residue was diluted with water, acidified with 1 N HCl and extracted with EtOAc. The EtOAc extract was washed twice with water, dried (Na2SO4) and concentrated to give the title compound as a yellow foam.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. customVolatile materials were removed in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc
  6. extractionThe EtOAc extract
  7. washwas washed twice with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-70a5d77146bc4ac4ad52e6448b1e0aae
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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