2-Pyridineacetic acid → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-[4-(2-pyridin-2-yl-acetoxymethyl)-phenyl]-propionic acid
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].ClC(Cl)(Cl)C[O:14][C:15](=[O:36])[CH:16]([S:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=1>>[F:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH2:27][S:26][CH:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][O:9][C:8](=[O:10])[CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:22][CH:23]=2)[C:15]([OH:36])=[O:14])=[CH:30][CH:31]=1Participants
3
Procedure
The title compound was prepared starting from 2-pyridineacetic acid (HCl salt) and 2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester in the same manner as described for example 7 (yield: 8.6 mg, 29%). 1H-NMR (300 MHz, CDCl3): δ 2.83-3.16 (m, 6H), 3.54-3.71 (m, 1H), 3.64 (s, 2H), 5.06-5.20 (m, 2H), 6.91-7.00 (m, 2H), 7.09-7.35 (m, 7H), 7.66 (brd, 1H), 8.06 (brs, 1H), 8.45 (brd, 1H); Mass Spectrum: M+H+ 455.
Sources & evidence
- ORD record
- ord-4070a87086324f11a3756911af420d5a
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181181B2
Reaction notes
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