3-(4-Hydroxyphenyl)propionic acid → N-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl]propanamide

HRID 1180174Notes

Reaction equation

HRID 1180174 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)=[CH:4][CH:3]=1.[OH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34](O)=[O:35])=[CH:28][CH:27]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)[C:34](=[O:35])[CH2:33][CH2:32][C:29]2[CH:30]=[CH:31][C:26]([OH:25])=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 23440828(4-Fluorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine

Product 1

HCID 23440768N-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl]propanamideYield 89%

Procedure

The title compound was prepared as described in Example 44. D using (4-fluorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine (1.4 g, 4.36 mmol) and 3-(4-hydroxyphenyl)propanoic acid (1.01 g, 6.11 mmol) to provide the title compound (1.82 g, 89% yield): ES-MS (m/z) 470 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ec6cfcad005d4fec83f010a3eed64bf4
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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