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

HRID 2186051Notes

Reaction equation

HRID 2186051 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3b1f27b42aeb4211a58bb9045cb7cbad
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

Loading…