(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester → (5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

HRID 655271노트

반응식

HRID 655271 반응식
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[C:9]([F:18])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)(C)(C)C>[OH-].[Na+]>[CH3:1][O:5][C:6](=[O:19])[CH2:7][C:8]1[C:9]([F:18])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

참가 물질

3

반응물 1

HCID 68530051(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester

생성물 1

HCID 68534543(5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester (5 g, 19 mmol) in 25 ml of aq. NaOH (4N) was heated to reflux for 4 h. The mixture was washed with ethyl acetate and the aqueous layer was acidified to pH 5 with conc. HCl. The resulting precipitate was collected and washed with water and dried in vacuo to return (5-fluoro-quinolin-6-yl)-acetic acid. To this solid was added conc.H2SO4 (1.2 ml) and MeOH (20 ml) and the solution heated to reflux for 6 h. After cooling the solvent was removed in vacuo and the residue purified by flash column chromatography to return the title compound (2.0 g 48%).

후처리

  1. temperatureto reflux for 4 h
  2. washThe mixture was washed with ethyl acetate
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuo
  6. additionTo this solid was added conc
  7. temperatureH2SO4 (1.2 ml) and MeOH (20 ml) and the solution heated
  8. temperatureto reflux for 6 h
  9. temperatureAfter cooling the solvent
  10. customwas removed in vacuo
  11. customthe residue purified by flash column chromatography

출처 및 근거

ORD 기록
ord-71da30cbf15b440ea3b2e9780eeb8075
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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