3-Fluoro-5-(trifluoromethyl)benzylamine → (2S)-2-ethoxy-3-{4-[1-(3-fluoro-5-trifluoromethyl-benzylcarbamoyl)-1-methyl-ethoxy]-phenyl}-propionic acid

HRID 1353241Notes

Reaction equation

HRID 1353241 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]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[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>>[CH2:21]([O:20][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([C:17](=[O:19])[NH:29][CH2:28][C:27]2[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=[C:25]([F:24])[CH:26]=2)([CH3:15])[CH3:16])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 27333043-Fluoro-5-(trifluoromethyl)benzylamineHCID 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 58646636(2S)-2-ethoxy-3-{4-[1-(3-fluoro-5-trifluoromethyl-benzylcarbamoyl)-1-methyl-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 3-fluoro-5-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 C23H25F4NO5 [M−H]−: 470.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-319bfbd44d21486589fdc4b447f26795
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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