2-[4-(Trifluoromethyl)phenyl]ethan-1-amine → (2S)-2-ethoxy-3-(4-{1-methyl-1-[2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid

HRID 1353240Notes

Reaction equation

HRID 1353240 reaction equation
C([O:3][C:4](=[O:23])[C@@H:5]([O:20][CH2:21][CH3:22])[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:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](CCN)=[CH:28][CH:27]=1.C(O[C@@H](CC1C=CC(O[C@@H:52]([C:54](=O)[NH:55]CCC2C=CC(OC3C=CC=CC=3)=CC=2)C)=CC=1)C(O)=O)C>>[CH2:21]([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][CH2:54][CH2:52][C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:31]=2)[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amineHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58646608(2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 10096124(2S)-2-ethoxy-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-ethoxy-propionic acid ethyl ester (EXAMPLE 49, step 2) and 2-(4-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 C24H28F3NO5 [M−H]−: 466.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-a672c10ae5114577b726ca0752e9c4c8
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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