3-(4-Carboxymethyl-phenyl)-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid 2,2,2-trichloro-ethyl ester → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-[4-(4-methanesulfonyloxy-benzyloxycarbonylmethyl)-phenyl]-propionic acid

HRID 1628178Notes

Reaction equation

HRID 1628178 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][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.O[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=1>>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][S:18][CH:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:37][CH:38]=3)=[O:16])=[CH:12][CH:13]=2)[C:5]([OH:4])=[O:28])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 668646303-(4-Carboxymethyl-phenyl)-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid 2,2,2-trichloro-ethyl esterHCID 85989572Methanesulfonic acid 4-hydroxymethyl-phenyl ester

Product 1

HCID 250946852-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-[4-(4-methanesulfonyloxy-benzyloxycarbonylmethyl)-phenyl]-propionic acid

Procedure

The title compound was prepared from 3-(4-carboxymethyl-phenyl)-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid 2,2,2-trichloro-ethyl ester (30 mg, 0.01 mmol) and methanesulfonic acid 4-hydroxymethyl-phenyl ester (14 mg, 0.067 mmol) in the same manner as described for example 1. The crude product was purified by HPLC (yield: 0.47 mg, 1.4%). Mass Spectrum: M−H+ 545.50.

Workup

  1. customThe crude product was purified by HPLC (yield: 0.47 mg, 1.4%)

Sources & evidence

ORD record
ord-48fb0f89cfbf4ecfadea52f90f5b8ba4
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

Loading…