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(Diethylamino)sulfur trifluoride → (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1051725
ノート
印刷プレビュー

反応式

HRID 1051725 の反応式
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15]([N:17]1[CH2:20][C:19]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[C:28]([O:42][CH:43]4[CH2:46][CH2:45][CH2:44]4)=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:37]([O:39][CH3:40])=[O:38])[C@@H:32]([CH3:41])[CH2:31][CH2:30]4)[N:26]=2)(O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>ClCCl>[C:10]([O:14][C:15]([N:17]1[CH2:20][C:19]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[C:28]([O:42][CH:43]4[CH2:46][CH2:45][CH2:44]4)=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:37]([O:39][CH3:40])=[O:38])[C@@H:32]([CH3:41])[CH2:31][CH2:30]4)[N:26]=2)([F:7])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 118076304(S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

生成物 1

HCID 118075426(S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate収率 59%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

(Diethylamino)sulfur trifluoride (DAST) (0.152 g, 0.94 mmol) was added to a −78° C. solution of (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.100 g, 0.19 mmol) in dichloromethane (4 mL), and the resulting solution stirred for 2 h at −78° C. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 30% ethyl acetate/petroleum ether) to afford (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.059 g, 59%) as a yellow solid. MS (ESI, pos. ion) m/z 532 [M+H]+.

後処理

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified via preparative thin layer chromatography (eluting with 30% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-8a94e2ec00bf472eb695fc4f75843269
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09388161B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート