Ibuprofen, (+-)- → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-{4-[2-(4-isobutyl-phenyl)-propionyloxymethyl]-phenyl}-propionic acid

HRID 709496Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].ClC(Cl)(Cl)C[O:19][C:20](=[O:41])[CH:21]([S:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=1>>[F:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][CH2:32][S:31][CH:21]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][O:13][C:12](=[O:14])[CH:11]([C:8]3[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=3)[CH3:15])=[CH:27][CH:28]=2)[C:20]([OH:41])=[O:19])=[CH:35][CH:36]=1

Participants

Reactant 2

HCID 3672Ibuprofen, (+-)-

HCID 441850462-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 250949602-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-{4-[2-(4-isobutyl-phenyl)-propionyloxymethyl]-phenyl}-propionic acid

Procedure

The title compound was prepared starting from 2-(4-isobutyl-phenyl)-propionic acid 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: 5.6 mg, 17%). 1H-NMR (300 MHz, CDCl3): δ 0.90 (d, 6H), 1.50 (d, 3H), 1.77-1.92 (m, 1H), 2.45 (d, 2H), 2.75-2.96 (m, 5H), 3.12-3.23 (m, 1H), 3.41-3.50 (m, 1H), 3.74 (q, 1H), 5.00-5.13 (m, 2H), 6.91-6.99 (m, 2H), 7.04-7.23 (m, 10H); Mass Spectrum: M−H+ 521.

Sources & evidence

ORD record: ord-4691dd6aa36c4e8aa9f68490e9e684b5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181181B2

Reaction notes

Loading…