Potassium Carbonate → (S)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061874ノート

反応式

HRID 2061874 の反応式
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.CN(C)/[CH:17]=[C:18](/[C:24](=[O:33])[C:25]1[CH:30]=[C:29]([I:31])[CH:28]=[CH:27][C:26]=1F)\[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>O>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@@H:3]([CH2:2][N:1]2[C:26]3[C:25](=[CH:30][C:29]([I:31])=[CH:28][CH:27]=3)[C:24](=[O:33])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17]2)[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2 回

生成物 1

HCID 86643631(S)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(S)-3-(Aminomethyl)-1-N-Boc-pyrrolidine (994 mg, 4.86 mmol) was added to the stock solution of (Z)-ethyl 3-(dimethylamino)-2-(3-iodobenzoyl)acrylate (Intermediate 24, 0.34M, 13 mL, 4.42 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was dried in a vacuum oven for 1.5 h. The resulting residue was then dissolved in dimethylformamide (8 mL) and potassium carbonate powder (670 mg, 4.86 mmol) was added. The reaction mixture was heated at 60° C. for overnight then cooled to room temperature. Water (50 mL) was added and the suspension was extracted with ethyl acetate (3×50 mL). The organic layers were dried over sodium sulfate, and the solvent was removed in vacuo to give quantitative (S)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate as a brown sticky solid.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was dried in a vacuum oven for 1.5 h
  3. dissolutionThe resulting residue was then dissolved in dimethylformamide (8 mL)
  4. temperatureThe reaction mixture was heated at 60° C. for overnight
  5. temperaturethen cooled to room temperature
  6. extractionthe suspension was extracted with ethyl acetate (3×50 mL)
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-fb408396afa84a1483524c77e85a3623
出典データセット
uspto-grants-2012_10
特許番号
US08283361B2

反応ノート

読み込み中…