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

HRID 2186051노트

반응식

HRID 2186051 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3b1f27b42aeb4211a58bb9045cb7cbad
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403578B1

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