3-Aminocinnamic acid ethyl ester → 3-(3-{[5-(3-Chloro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

HRID 2053178Notes

Reaction equation

HRID 2053178 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:16]([O:18][C:19](=[O:29])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1)[CH3:17]>>[CH2:16]([O:18][C:19](=[O:29])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:13]([C:11]2[O:12][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[CH:9][CH:10]=2)=[O:15])[CH:23]=1)[CH3:17]

Participants

3

Reactant 2

HCID 978253-Aminocinnamic acid ethyl esterHCID 7362565-(3-Chlorophenyl)furan-2-carboxylic acid

Product 1

HCID 684907963-(3-{[5-(3-Chloro-phenyl)-furan-2-carbonyl]-amino}-phenyl)-acrylic acid ethyl ester

Procedure

Carboxylic acid (65) (58 mg, 0.26 mmol) was coupled to ethyl ester (60) (50 mg, 0.26 mmol) using Method C. The crude residue was purified by column chromatography eluting with a stepped gradient of 10-15% EtOAc in heptane to give the title compound.

Workup

  1. customThe crude residue was purified by column chromatography
  2. washeluting with a stepped gradient of 10-15% EtOAc in heptane

Sources & evidence

ORD record
ord-3353e5b8599946d697dc8e60a31d317c
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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