Sodium Hydroxide → Gsk-269984A

HRID 2356618

Reaktionsgleichung

Reaktionsgleichung von HRID 2356618
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[F:29])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[OH-].[Na+:31]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[F:29])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O-:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[Na+:31]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59384237Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

Produkt 1

HCID 23696973Gsk-269984A

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-2-pyridinecarboxylate (2 g) was dissolved in ethanol (15 ml) at reflux. 2M Sodium hydroxide (3.4 ml) was added and the solution heated under reflux for 30 minutes. No residual starting material by HPLC. The solution was filtered and the filter washed with a mixture of hot ethanol (5 ml) and water (5 ml). The combined filtrate and wash were re-heated to reflux, and water (15 ml) added dropwise over ˜5 minutes and the clear solution allowed to cool slowly to room temperature. The product crystallised rapidly at ˜35° C. The resulting thick suspension was cooled to 20-25° C. and stirred for 1 hour. The product was isolated and washed with 1:3 ethanol:water (20 ml) and then dried overnight at 50° C. in vacuo to give the title compound (1.94 g).

Aufarbeitung

  1. temperatureat reflux
  2. temperaturethe solution heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationThe solution was filtered
  5. washthe filter washed with a mixture of hot ethanol (5 ml) and water (5 ml)
  6. washThe combined filtrate and wash
  7. temperaturewere re-heated
  8. temperatureto reflux
  9. additionwater (15 ml) added dropwise over ˜5 minutes
  10. customThe product crystallised rapidly at ˜35° C
  11. temperatureThe resulting thick suspension was cooled to 20-25° C.
  12. customThe product was isolated
  13. washwashed with 1:3 ethanol
  14. dry with materialwater (20 ml) and then dried overnight at 50° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b2973bc9068e45339ab308432797ce78
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759369B2

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