3-(Trifluoromethyl)benzylamine → (2S)-2-methoxy-3-{4-[1-methyl-1-(3-trifluoromethyl-benzylcarbamoyl)-ethoxy]-phenyl}-propionic acid

HRID 1353233Notes

Reaction equation

HRID 1353233 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:34])([F:33])[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH2:29].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][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:29][CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[C:25]([C:24]([F:23])([F:33])[F:34])[CH:26]=2)[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:22]

Participants

4

Reactant 3

HCID 759623-(Trifluoromethyl)benzylamineHCID 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 58646605(2S)-2-methoxy-3-{4-[1-methyl-1-(3-trifluoromethyl-benzylcarbamoyl)-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 3-trifluoromethyl-benzylamine 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 C22H24F3NO5 [M−H]−: 438.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-aeb9d74bd8554b4f9a62c9362fc70f28
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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