Diethyl Pyrocarbonate → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]prop-2-enamide

HRID 1479822

反応式

HRID 1479822 の反応式
[CH2:1]([N:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4](=[CH2:8])[C:5]([OH:7])=O)[CH3:2].CCOC(OC(OCC)=O)=O.[F:30][C:31]([F:48])([F:47])[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[C:41]([CH2:45][NH2:46])[CH:42]=[CH:43][CH:44]=2)=[CH:35][CH:34]=1>C1COCC1>[CH2:1]([N:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4](=[CH2:8])[C:5]([NH:46][CH2:45][C:41]1[CH:42]=[CH:43][CH:44]=[C:39]([C:36]2[CH:37]=[CH:38][C:33]([O:32][C:31]([F:30])([F:47])[F:48])=[CH:34][CH:35]=2)[CH:40]=1)=[O:7])[CH3:2]

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 61032752(4'-(Trifluoromethoxy)-[1,1'-biphenyl]-3-yl)methanamineHCID 903842012-[Ethyl-(4-fluorophenyl)sulfonyl-amino]prop-2-enoic acid

生成物 1

HCID 783202182-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]prop-2-enamide収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of acid 4B (0.35 g, 1.28 mmol) in THF (25 mL) was added with DEPC (0.25 mL, 1.3 mol eq) and the mixture was stirred at room temperature for 10′. Then [3-[4-(trifluoromethoxy)phenyl]phenyl]methanamine 23B (0.376 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, water (40 mL) was added to the residue that is extracted with EtOAc (3×25 mL) and washed with brine (1×40 mL). The separated organic phase was anydrified over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a white solid (0.15 g) after recrystallization from ethyl ether. Yield=24%, 1HNMR (DMSO, 200 MHz) δ 1.08 (t, 3H, J=8), 3.37 (q, 2H, J=7.5), 4.44 (d, 2H, J06.1), 5.16 (s, 1H), 6.09 (s, 1H), 7.32 (d, 1H), 7.46 (m, 5H), 7.53 (d, 1H), 7.62 (s, 1H), 7.76 (dd, 2H), 7.86 (m, 2H), 8.78 (t, 1H); [M+1] 522.51 (C25H22F4N2O4S requires 522.12).

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure, water (40 mL)
  3. additionwas added to the residue that
  4. extractionis extracted with EtOAc (3×25 mL)
  5. washwashed with brine (1×40 mL)
  6. customevaporated to dryness
  7. customthe residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether)

出典と根拠

ORDレコード
ord-71898a139293460d905e0d816cdbf629
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

関連ノート

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