Ethyl 3-amino-3-phenylprop-2-enoate → t-butyl 2-[N-[1,4-dihydro-2-methyl-5-methoxycarbonyl-4-(3-nitrophenyl)-6-phenylpyridine-3-carbonyl]amino]acetate

HRID 963674Notes

Reaction equation

HRID 963674 reaction equation
[C:1]([C:4](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:6])(=O)[CH3:2].[NH2:26][C:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[CH:28][C:29]([O:31][CH2:32]C)=[O:30]>>[CH3:2][C:1]1[NH:26][C:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:28]([C:29]([O:31][CH3:32])=[O:30])[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:4]=1[C:5]([NH:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:6]

Participants

3

Reactant 2

HCID 312934Ethyl 3-amino-3-phenylprop-2-enoateHCID 53908936t-butyl 2-[N-[2-(3-nitrobenzylidene)-3-oxobutanoyl]amino]acetate

Product 1

HCID 70073479t-butyl 2-[N-[1,4-dihydro-2-methyl-5-methoxycarbonyl-4-(3-nitrophenyl)-6-phenylpyridine-3-carbonyl]amino]acetateYield 22%

Conditions

Temperature
110 °C

Procedure

More specifically a mixture of 330 mg (1 mmol) of t-butyl 2-[N-[2-acetyl-3-(3-nitrophenyl)-2-propenoyl]amino]acetate and 191 mg (1 mmol) of ethyl 3-amino-3-phenyl-2-propenoate was stirred under a light-shielding condition at 110° C. overnight. After cooling to room temperature, the reaction mixture was chromatographed on a silica gel column for purification, whereby 98 mg (22%) of the captioned compound was obtained as an oily material.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was chromatographed on a silica gel column for purification

Sources & evidence

ORD record
ord-e01ea124bad446eda58447db97f95412
Source dataset
uspto-grants-1998_06
Patent number
US05763614

Reaction notes

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