Diethyl Pyrocarbonate → 1-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]cyclopropanecarboxamide

HRID 1479853ノート

反応式

HRID 1479853 の反応式
[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:4]1([C:7]([OH:9])=O)[CH2:6][CH2:5]1)[CH3:2].CCOC(OC(OCC)=O)=O.[F:31][C:32]([F:49])([F:48])[O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:41]=[C:42]([CH2:46][NH2:47])[CH:43]=[CH:44][CH:45]=2)=[CH:36][CH:35]=1>C1COCC1>[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:4]1([C:7]([NH:47][CH2:46][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([C:37]3[CH:38]=[CH:39][C:34]([O:33][C:32]([F:31])([F:48])[F:49])=[CH:35][CH:36]=3)[CH:41]=2)=[O:9])[CH2:5][CH2:6]1)[CH3:2]

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 61032752(4'-(Trifluoromethoxy)-[1,1'-biphenyl]-3-yl)methanamineHCID 903843631-[Ethyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylic acid

生成物 1

HCID 903841351-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]cyclopropanecarboxamide収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of acid 15A (0.30 g, 1.8 mmol) in THF (20 mL) was added with DEPC (0.21 mL, 1.3 mol eq) and the mixture was stirred at room temperature for 10 minutes. Then [3-[4-(trifluoromethoxy)phenyl]phenyl]methanamine 23B (0.308 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc (45 mL) and washed with water (50 mL) and brine. The separated organic phase was dried over an. Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a white solid (0.15 g). Yield=28%, 1HNMR (DMSO, 200 MHz) δ 1.08 (m, 2H), 1.20 (t, 3H, J=8), 1.38 (bs, 2H), 3.42 (q, 2H), 4.38 (d, 2H, J=5.6), 7.27 (d, 1H, J=4), 7.46-7.39 (m, 6H), 7.55 (d, 1H), 7.59 (s, 1H), 7.78 (m, 2H), 7.87 (m, 2H), 8.08 (t, 1H). [M+1] 536.54 (C26H24F4N2O4S requires 536.14).

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water (50 mL) and brine
  4. customThe separated organic phase was dried over an
  5. customNa2SO4 and evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether)

出典と根拠

ORDレコード
ord-20beefd84e6c44b2aea8284ed3e699d2
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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