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

HRID 561204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561204
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70a5d77146bc4ac4ad52e6448b1e0aae
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

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