Triethylamine → methyl N-[2-Nitro-4-(t-butoxycarbonyl)benzyl]-N-phenylethyl-4-aminocrotonate

HRID 2186051ノート

反応式

HRID 2186051 の反応式
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].[C:19]1([CH2:25][CH2:26][NH:27][CH2:28]/[CH:29]=[CH:30]/[C:31]([O:33][CH3:34])=[O:32])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8][C:5]=1[CH2:6][N:27]([CH2:26][CH2:25][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:28]/[CH:29]=[CH:30]/[C:31]([O:33][CH3:34])=[O:32])([O-:3])=[O:2]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 18462578t-Butyl 4-bromomethyl-3-nitrobenzoateHCID 23291030Methyl 4-(phenylethylamino)crotonate

生成物 1

HCID 10837430methyl N-[2-Nitro-4-(t-butoxycarbonyl)benzyl]-N-phenylethyl-4-aminocrotonate収率 88.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-nitro-4-(t-butoxycarbonyl)-benzylbromide (4.06 g, 12.8 mmol) in THF (50 mL), methyl 4-(phenylethylamino)-crotonate (3.4 g, 15.5 mmol) was added with stirring at RT. Triethylamine (2.2 mL, 15.7 mmol) was then added. After stirring for 16 h, the reaction was diluted with ethyl acetate and washed with 1N sodium carbonate, brine, dried (sodium sulfate) and concentrated. Flash chromatography (silica gel, 15% ethyl acetate/n-hexane) gave the title compound as an oil (5.16 g, 88%). 1H-NMR (CDCl3) δ1.60(9H, s), 2.74(4H, br s), 3.30(2H, dd), 3.74(3H, s), 4.00(2H, s), 6.00(1H, d, J=15 Hz), 7.02(1H, dt), 7.25(5H, m), 7.67(1H, d, J=8 Hz), 8.15(1H, dd), 8.45(1H, d, J=2 Hz).

後処理

  1. stirringAfter stirring for 16 h
  2. washwashed with 1N sodium carbonate, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-3b1f27b42aeb4211a58bb9045cb7cbad
出典データセット
uspto-grants-2002_06
特許番号
US06403578B1

反応ノート

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