Reaktion #1679196

Reaktionsgleichung

2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

3-methoxycarbonyl phenylboronic acid

→

3-[5-(2,4-dimethoxybenzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]benzoic acid methyl ester

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent is evaporated
2. 2
   SonstigeThe residue is partitioned between EtOAc and 1N aqueous HCl
3. 3
   TrocknenThe organic layer is dried over anhydrous Na2SO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigechromatographed on silica gel using 30% EtOAc in hexanes as the eluent

Vorschrift

A solution of the title B compound in Example 36, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (115 mg, 4.02 mmol) and 3-methoxycarbonyl phenylboronic acid (145 mg, 8.04 mmol) in 1,4-dioxane (5 mL) is treated with copper(II) acetate (110 mg, 6.03 mmol) and CS2CO3 (262 mg, 8.04 mmol). The mixture is stirred at RT for 16 h and the solvent is evaporated. The residue is partitioned between EtOAc and 1N aqueous HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated. The residue is flash chromatographed on silica gel using 30% EtOAc in hexanes as the eluent to give 3-[5-(2,4-dimethoxybenzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]benzoic acid methyl ester as a clear oil: [M+NH4]+=438.

Quelle