Ethyl 2-(3-aminophenoxy)acetate → (3-{[5-(3-Chloro-phenyl)-furan-2-carbonyl]-amino}-phenoxy)-acetic acid ethyl ester

HRID 2053176Notes

Reaction equation

HRID 2053176 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])[CH2:20][O: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])[CH2:20][O: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 412308Ethyl 2-(3-aminophenoxy)acetateHCID 7362565-(3-Chlorophenyl)furan-2-carboxylic acid

Product 1

HCID 59654640(3-{[5-(3-Chloro-phenyl)-furan-2-carbonyl]-amino}-phenoxy)-acetic acid ethyl ester

Procedure

Carboxylic acid (65) (67 mg, 0.3 mmol) was coupled to ethyl ester (64) (58 mg, 0.25 mmol) using Method C. The crude residue was purified by column chromatography eluting with a stepped gradient of 10-20% 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 10-20% EtOAc in heptane

Sources & evidence

ORD record
ord-985823996b574632bbff8b33009b3daf
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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