4-(4-Fluorobenzoyl)piperidine → (2S)-3-(4-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-2-oxo-ethoxy}-phenyl)-2-methoxy-propionic acid

HRID 1353218Notes

Reaction equation

HRID 1353218 reaction equation
C([O:3][C:4](=[O:20])[C@@H:5]([O:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([OH:17])=O)=[CH:9][CH:8]=1)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:29])=[CH:24][CH:23]=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>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([CH:30]2[CH2:35][CH2:34][N:33]([C:15](=[O:17])[CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:18][CH3:19])[C:4]([OH:3])=[O:20])=[CH:12][CH:11]=3)[CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58864673(2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

Product 1

HCID 58646601(2S)-3-(4-{2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-2-oxo-ethoxy}-phenyl)-2-methoxy-propionic acid

Procedure

The title compound was prepared from (2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (PREPARATION 3, step 2) and (4-fluoro-phenyl)-piperidin-4-yl-methanone 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 C24H26FNO6 [M+H]+: 444.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-91395ebfbb3845799914344448d8beeb
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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