Hydrochloric Acid → HCID 10392180、化合物

HRID 1708550ノート

反応式

HRID 1708550 の反応式
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:19])[C:17]=1[F:18])[N:14]([NH:20][CH3:21])[CH:13]=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:11]2=[O:27].[C:28]([O:32][C:33]([C:35](=[CH2:43])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:34])([CH3:31])([CH3:30])[CH3:29].Cl>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:19])[C:17]=1[F:18])[N:14]([N:20]([CH3:21])[CH2:43][CH:35]([C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:13]=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:11]2=[O:27]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11096368Propanedioic acid, methylene-, bis(1,1-dimethylethyl) esterHCID 11098599Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 10392180HCID 10392180、化合物収率 38.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Solid potassium tert-butoxide (823 mg) was added to tetrahydrofuran (40 ml) solution of ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (2.0 g) and tert-butyl 2-tert-butoxycarbonylacrylate (1.67 g), with stirring and suspending under ice-cooling, and the suspension was stirred for 0.5 hour with ice-cooling and then 1.5 hours at room temperature. The reaction solution was poured into a mixed liquid of ethyl acetate ice-water (150 ml/150 ml) and was adjusted to have pH of 3.0 with 1N hydrochloric acid. The organic layer was separated out, washed with water and saline solution, and dried over magnesium sulfate. This was concentrated under reduced pressure to obtain an amorphous product. The amorphous product was subjected to column chromatography with silica gel and eluted with a mixed solvent of methylene chloride ethyl acetate (20/1 to 10/1). The fractions containing the object product were collected, and the solvent was removed by distillation under reduced pressure. The residue was tritulated with n-hexane, and the precipitates were filtered out to obtain ethyl 6,7,8-trifluoro-1 -[N-methyl-N-{2,2-bis(tert-butoxycarbonyl)ethyl}amino]-1,4 -dihydro-4-oxoquinoline-3-carboxylate (1.35 g) as an almost white powder.

後処理

  1. temperaturecooling
  2. stirringthe suspension was stirred for 0.5 hour with ice-
  3. temperaturecooling
  4. custom1.5 hours
  5. customat room temperature
  6. customThe organic layer was separated out
  7. washwashed with water and saline solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationThis was concentrated under reduced pressure
  10. customto obtain an amorphous product
  11. washeluted with a mixed solvent of methylene chloride ethyl acetate (20/1 to 10/1)
  12. additionThe fractions containing the object product
  13. customwere collected
  14. customthe solvent was removed by distillation under reduced pressure
  15. filtrationthe precipitates were filtered out

出典と根拠

ORDレコード
ord-cc52d0db44804173b2bdfe54b6fd9ff0
出典データセット
uspto-grants-1994_10
特許番号
US05359066

反応ノート

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