(4-Aminophenoxy)benzene → (2S)-2-methoxy-3-(4-{1-methyl-1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid

HRID 1353230Notes

Reaction equation

HRID 1353230 reaction equation
C([O:3][C:4](=[O:22])[C@@H:5]([O:20][CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15])=[CH:9][CH:8]=1)C.O(C1C=CC(N)=CC=1)C1C=CC=CC=1.C(O[C@@H](CC1C=CC(O[C@@H](C(=O)[NH:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][C:61]([O:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:60][CH:59]=2)C)=CC=1)C(O)=O)C>>[CH3:21][O:20][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([CH3:15])([C:17](=[O:19])[NH:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][C:61]([O:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:60][CH:59]=2)[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:22]

Participants

4

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58646603(2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 10367745(2S)-2-methoxy-3-(4-{1-methyl-1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (PREPARATION 5, step 2) and 4-phenoxy-phenylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a colorless oil. MS (ES) for C28H31NO6 [M+H]+: 478.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-d3301daa5a4049cd86e4632dfb2161d0
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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