Sodium Hydroxide → Gsk-269984A

HRID 2356619

반응식

HRID 2356619 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 23696973Gsk-269984A

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-2-pyridinecarboxylate (204.7 g) was dissolved in ethanol (1.5 L) and stirred under nitrogen at reflux until all the starting material is in solution. 2M Sodium hydroxide (355 ml) was added and the solution heated under reflux for 1 hr 10 minutes. HPLC showed that there was no residual starting material. The solution was filtered and the filter washed with a ˜1:1 mixture of hot ethanol (515 ml) and water (520 ml). The combined filtrate and wash were re-heated to reflux, and water (1.5 L) was added slowly over 5 minutes. The solution was then cooled to 20+/−5° C. over 2 hours and stirred for 1 hour. The product was then filtered off and washed with ethanol:water (1:1, 1030 ml), then ethanol:water (˜1:3; 385 ml ethanol:1.15 L water). The resulting solid was dried to a constant weight at 60° C. under vacuum, to give the title compound. (186 g).

후처리

  1. temperatureat reflux until all the starting material
  2. temperaturethe solution heated
  3. temperatureunder reflux for 1 hr 10 minutes
  4. filtrationThe solution was filtered
  5. washthe filter washed with a ˜1:1 mixture of hot ethanol (515 ml) and water (520 ml)
  6. washThe combined filtrate and wash
  7. temperaturewere re-heated
  8. temperatureto reflux
  9. additionwater (1.5 L) was added slowly over 5 minutes
  10. temperatureThe solution was then cooled to 20+/−5° C. over 2 hours
  11. stirringstirred for 1 hour
  12. filtrationThe product was then filtered off
  13. washwashed with ethanol:water (1:1, 1030 ml)
  14. customThe resulting solid was dried to a constant weight at 60° C. under vacuum

출처 및 근거

ORD 기록
ord-23c5dface5d34f8a82a808ac6dd77502
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759369B2

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