2-[4-(Methanesulfonyloxy)phenyl]acetic acid → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-{3-[2-(4-methanesulfonyloxy-phenyl)-acetoxy]-propyl}-phenyl)-propionic acid

HRID 709495Notes

Reaction equation

HRID 709495 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=[O:28])[CH:6]([S:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16]O)=[CH:10][CH:9]=1.[CH3:31][S:32]([O:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43]([OH:45])=[O:44])=[CH:38][CH:37]=1)(=[O:34])=[O:33]>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][S:18][CH:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][O:44][C:43](=[O:45])[CH2:42][C:39]3[CH:38]=[CH:37][C:36]([O:35][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:41][CH:40]=3)=[CH:12][CH:13]=2)[C:5]([OH:28])=[O:4])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 288754632-[4-(Methanesulfonyloxy)phenyl]acetic acidHCID 66864918HCID 66864918, compound

Product 1

HCID 250949582-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-{3-[2-(4-methanesulfonyloxy-phenyl)-acetoxy]-propyl}-phenyl)-propionic acid

Procedure

The title compound was prepared from 2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-3-[4-(3-hydroxy-propyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester (45 mg, 0.091 mmol) and (4-methanesulfonyloxy-phenyl)-acetic acid (19 mg, 0.083 mmol) in the same manner as described for example 1. The crude product was purified by HPLC (yield: 3.0 mg, 4.2%). 1H NMR (400 MHz, CDCl3): δ 7.30-7.32 (d, 2H), 7.21-7.23 (d, 2H), 7.05-7.08 (m, 4H), 6.98-7.00 (d, 2H), 6.90-6.94 (t, 2H), 4.04-4.07 (t, 2H), 3.63 (m, 2H), 3.46 (m, 2H), 3.08 (s, 3H), 2.79-2.90 (m, 5H), 2.54-2.58 (t, 2H), 1.87-1.90 (t, 2H).

Workup

  1. customThe crude product was purified by HPLC (yield: 3.0 mg, 4.2%)

Sources & evidence

ORD record
ord-7aa0fd61ad6f4ef7ba090789d755223f
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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