Phenethylamine, m-trifluoromethyl- → 2-Methoxy-3-(4-{1-methyl-1-[2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid

HRID 1353232Notes

Reaction equation

HRID 1353232 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.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH2:31][CH2:32][NH2:33])[CH:28]=[CH:29][CH:30]=1.C(O[C@@H](CC1C=CC(O[C@@H](C(=O)NCCC2C=CC(OC3C=CC=CC=3)=CC=2)C)=CC=1)C(O)=O)C>>[CH3:21][O:20][CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([CH3:15])([C:17](=[O:19])[NH:33][CH2:32][CH2:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=2)[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:22]

Participants

4

Reactant 3

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 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 694180062-Methoxy-3-(4-{1-methyl-1-[2-(3-trifluoromethyl-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 2-(3-trifluoromethyl-phenyl)-ethylamine 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 C23H26F3NO5 [M−H]−: 452.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-29b83ee6cc7f4999bd18d7fba4286df4
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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