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

HRID 709492Notes

Reaction equation

HRID 709492 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=[O:26])[CH:6]([S:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.[CH3:29][S:30]([O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41](O)=[O:42])=[CH:36][CH:35]=1)(=[O:32])=[O:31]>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][S:16][CH:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][O:15][C:41](=[O:42])[CH2:40][C:37]3[CH:36]=[CH:35][C:34]([O:33][S:30]([CH3:29])(=[O:31])=[O:32])=[CH:39][CH:38]=3)=[CH:12][CH:13]=2)[C:5]([OH:4])=[O:26])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 288754632-[4-(Methanesulfonyloxy)phenyl]acetic acidHCID 441850462-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 250946832-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-{4-[2-(4-methanesulfonyloxy-phenyl)-acetoxymethyl]-phenyl}-propionic acid

Procedure

The title compound was prepared from 2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2 trichloro-ethyl ester (33 mg, 0.072 mmol) and (4-methanesulfonyloxy-phenyl)-acetic acid (15 mg, 0.065 mmol) in the same manner as described for example 1. The crude product was purified by flash chromatography (yield: 2.0 mg, 5.6%). Mass Spectrum: M+H+ 547.10.

Workup

  1. customThe crude product was purified by flash chromatography (yield: 2.0 mg, 5.6%)

Sources & evidence

ORD record
ord-2b39e81d6246430d81992b9273fd6b35
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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